Supporting Information
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1 Supporting Information Cyclization of Ketones with Nitriles under Base: A General and Economical Synthesis of Pyrimidines Lebin Su, Kang Sun, Neng Pan, Long Liu, Mengli Sun, Jianyu Dong,* Yongbo Zhou,* and Shuang-Feng Yin State Key Laboratory of Chemo/Biosensing and Chemometrics, College of Chemistry and Chemical Engineering, Hunan University, Changsha, , People s Republic of China djyustc@hotmail.com; zhouyb@hnu.edu.cn Table of Contents 1. General Information S2 2. General Experimental Procedure S2 3. Characterization Data for the Products S4-S18 4. References S18 5. Copies of 1 H and 13 C NMR Spectra of the Products S19-S59 S1
2 1. General information The reactions were carried out in schlenk tubes of 10 ml under N 2 atmosphere. Reagents were used as received unless otherwise noted, and solvents were purified according to standard operation procedure. Column chromatography was performed using Silica Gel 60 ( mesh). The reactions were monitored by GC and GC-MS, GC-MS results were recorded on GC-MS QP2010, and GC analysis was performed on GC 2014 plus. The 1 H and 13 C NMR spectra were recorded on a Brucker ADVANCE III spectrometer at 400 MHz and 100 MHz respectively, and chemical shifts were reported in parts per million (ppm). The electron ionization (EI) method was used as the ionization method for the HRMS measurement, and the mass analyzer type is TOF for EI. All solvents and reagents were purchased from Energy Chemical, Alfa Aesar, and Aladdin. 2. General Experimental Procedure a) General Experimental Procedure for the Synthesis of Pyrimidines An oven dried Schlenk tube of 10 ml equipped with a magnetic stir bar was charged with CuCl 2 (20 mol %) and NaOH (0.6 mmol, 2.0 equiv), ketone 1 (0.30 mmol), nitrile 2 (0.6 ml) were added. The reaction mixture was heated at 120 C for 24 h under N 2. After completion of the reaction, the reaction mixture was cooled to room temperature. Then washed with saturated NH 4 Cl aqueous solution (5.0 ml), and extracted with ethyl acetate (3 5 ml), and the organic layer was dried over anhydrous Na 2 SO 4 and was concentrated under vacuum. The desired product 3 was isolated by column chromatography (eluent: ethyl acetate/petroleum ether = 1/20 1/10) over silica gen ( mesh) using petroleum ether-ethyl acetate as eluent. Table S1. Optimization of Conditions a entry cat. base temp ( C ) conv (%) b yield (%) c yield (%) c 3a 3a' S2
3 1 CuI NaOH CuCl NaOH CuBr NaOH CuCl 2 NaOH CuBr 2 NaOH Cu(OAc) 2 NaOH Cu(OH) 2 NaOH CuO NaOH ZnCl 2 NaOH nd AgOTf NaOH nd FeCl 3 NaOH nd CoBr 2 NaOH nd CuCl 2 t-buona CuCl 2 t-buok CuCl 2 KOH CuCl 2 Na 2 CO <5 nd 0 17 CuCl 2 Et 3 N nd 0 18 CuCl nd 0 19 CuCl 2 NaOH CuCl 2 NaOH a Reaction conditions: 1a (0.3 mmol), catalyst (0.06 mmol, 20 mol %), base (0.6 mmol, 2 equiv) in CH 3 CN 2a (0.6 ml) for 24 h under N 2. b conversion of 2a. c GC yields using n-tridecane as an internal standard. b) General Experimental Procedure for Large Scale Reaction An oven dried Schlenk tube of 100 ml equipped with a magnetic stir bar was charged with CuCl 2 (20 mol %) and NaOH (18 mmol, 2.0 equiv), ketone 1b (9 mmol), nitrile 2c (18 ml), were added. The reaction mixture was heated at 120 C for 30 h. After completion of the reaction, the reaction mixture was cooled to room temperature. The crude product was extracted with ethyl acetate (3 25 ml), and the organic layer was dried over anhydrous S3
4 Na 2 SO 4 and was concentrated under vacuum. The residue was purified by column chromatography on silica gel and eluted with petroleum ether/ethyl acetate (40/1) to afford 3y in 82% yield (2.400 g). 3. Characterization Data for the Products 2,4-dimethyl-6-phenylpyrimidine (3a) 1 silica gel to afford a yellow oil in 78% yield (43.0 mg). 1 H NMR (400 MHz, CDCl 3 ): δ (m, 2H), (m, 3H), 7.35 (s, 1H), 2.75 (s, 3H), 2.54 (s, 3H). 13 C NMR (100 MHz, CDCl 3 ): δ 167.9, 167.2, 163.9, 137.2, 130.5, 128.8, 127.1, 113.4, 26.2, (4-fluorophenyl)-2,6-dimethylpyrimidine (3b) silica gel to afford a yellow solid in 85% yield (51.5 mg). mp ºC; 1 H NMR (400 MHz, CDCl 3 ): δ 8.05 (dd, J = 8.4, 5.2 Hz, 2H), 7.32 (s, 1H), 7.16 (t, J = 8.6 Hz, 2H), 2.74 (s, 3H), 2.54 (s, 3H). 13 C NMR (100 MHz, CDCl 3 ): δ 168.0, 167.4, (d, J = Hz), 162.8, (d, J = 3.0 Hz), (d, J = 8.6 Hz), 115.9(d, J = 21.6 Hz), 113.0, 26.2, HRMS (EI) m/z: [M] + calcd for C 12 H 11 FN 2 : found, ,4-dimethyl-6-(4-(trifluoromethyl)phenyl)pyrimidine (3c) silica gel to afford a yellow oil in 87% yield (65.8 mg). 1 H NMR (400 MHz, CDCl 3 ): δ 8.15 (d, J = 8.2 Hz, 2H), S4
5 7.73 (d, J = 8.2 Hz, 2H), 7.39 (s, 1H), 2.77 (s, 3H), 2.57 (s, 3H). 13 C NMR (100 MHz, CDCl 3 ): δ 168.2, 167.9, 162.4, 140.6, (d, J = 32.5 Hz), 127.5, (q, J = 3.7 Hz), 122.6, 113.7, 26.1, HRMS (EI) m/z: [M] + calcd for C 13 H 11 F 3 N 2 : found, (4-chlorophenyl)-2,6-dimethylpyrimidine (3d) silica gel to afford a yellow solid in 82% yield (53.6 mg). mp ºC ; 1 H NMR (400 MHz, CDCl 3 ): δ 7.97 (d, J = 8.5 Hz, 2H), 7.42 (d, J = 8.5 Hz, 2H), 7.29 (s, 1H), 2.72 (s, 3H), 2.52 (s, 3H). 13 C NMR (100 MHz, CDCl 3 ): δ 168.0, 167.5, 162.6, 137.2, 136.7, 135.5, 129.0, 128.4, 26.1, HRMS (EI) m/z: [M] + calcd for C 12 H 11 ClN 2 : found, ,4-dimethyl-6-(p-tolyl)pyrimidine (3e) silica gel to afford a yellow oil in 72% yield (42.8 mg). 1 H NMR (400 MHz, CDCl 3 ): δ 7.95 (d, J = 8.4 Hz, 2H), 7.34 (s, 1H), 7.28 (d, J = 8.0 Hz, 2H), 2.75 (s, 3H), 2.53 (s, 3H), 2.41 (s, 3H). 13 C NMR (100 MHz, CDCl 3 ): δ 167.9, 167.1, 164.0, 140.9, 134.4, 129.6, 127.1, 113.1, 26.2, 24.3, HRMS (EI) m/z: [M] + calcd for C 13 H 14 N 2 : found, (4-(tert-butyl)phenyl)-2,6-dimethylpyrimidine (3f) silica gel to afford a yellow oil in 65% yield (46.8 mg). 1 H NMR (400 MHz, CDCl 3 ): δ 7.97 (d, J = 8.4 Hz, 2H), S5
6 7.49 (d, J = 8.4 Hz, 2H), 7.33 (s, 1H), 2.74 (s, 3H), 2.53 (s, 3H), 1.35 (s, 9H). 13 C NMR (100 MHz, CDCl 3 ): δ 167.8, 167.0, 164.0, 154.0, 134.4, 126.9, 125.8, 113.1, 34.8, 31.2, 26.2, HRMS (EI) m/z: [M] + calcd for C 16 H 20 N 2 : found, (4-methoxyphenyl)-2,6-dimethylpyrimidine (3g) silica gel to afford a yellow oil in 68% yield (43.6 mg). 1 H NMR (400 MHz, CDCl 3 ): δ 8.02 (d, J = 8.8 Hz, 2H), 7.29 (s, 1H), 6.98 (d, J = 8.8 Hz, 2H), 3.85 (s, 3H), 2.72 (s, 3H), 2.51 (s, 3H). 13 C NMR (100 MHz, CDCl 3 ): δ 167.7, 166.9, 163.4, 161.7, 129.6, 128.6, 114.2, 112.4, 55.3, 26.2, HRMS (EI) m/z: [M] + calcd for C 13 H 14 N 2 O: found, ,4-dimethyl-6-(4-(methylthio)phenyl)pyrimidine (3h) silica gel to afford a yellow solid in 71% yield (49.0 mg). mp ºC ; 1 H NMR (400 MHz, CDCl 3 ): δ 7.97 (d, J = 8.4 Hz, 2H), (m, 2H), 7.30 (s, 1H), 2.73 (s, 3H), 2.52 (s, 3H), 2.51 (s, 3H). 13 C NMR (100 MHz, CDCl 3 ): δ 167.9, 167.2, 163.2, 142.2, 133.5, 127.4, 126.0, 112.7, 26.2, 24.3, HRMS (EI) m/z: [M] + calcd for C 13 H 14 N 2 S: found, ,4-dimethyl-6-(4-(methylsulfonyl)phenyl)pyrimidine (3i) S6
7 silica gel to afford a white solid in 70% yield (55.0 mg). mp ºC ; 1 H NMR (400 MHz, CDCl 3 ): δ 8.24 (d, J = 8.2 Hz, 2H), 8.05 (d, J = 8.2 Hz, 2H), 7.42 (s, 1H), 3.08 (s, 3H), 2.77 (s, 3H), 2.58 (s, 3H). 13 C NMR (100 MHz, CDCl 3 ): δ 168.3, 168.1, 161.8, 142.4, 141.9, 128.1, 127.9, 114.0, 44.5, 26.1, HRMS (EI) m/z: [M] + calcd for C 13 H 14 N 2 O 2 S: found, (3,5-bis(benzyloxy)phenyl)-2,6-dimethylpyrimidine (3j) silica gel to afford a yellow solid in 67% yield (79.6 mg). mp ºC; 1 H NMR (400 MHz, CDCl 3 ): δ 7.46 (d, J = 7.4 Hz, 4H), 7.40 (t, J = 7.3 Hz, 4H), (m, 5H), 6.74 (s, 1H), 5.11 (s, 4H), 2.77 (s, 3H), 2.54 (s, 3H). 13 C NMR (100 MHz, CDCl 3 ): δ 167.8, 167.3, 163.5, 160.3, 139.3, 136.6, 128.6, 128.0, 127.6, 113.5, 106.4, 104.2, 70.2, 26.2, HRMS (EI) m/z: [M] + calcd for C 26 H 24 N 2 O 2 : found, (2,6-dimethylpyrimidin-4-yl)aniline (3k) silica gel to afford a yellow oil in 73% yield (43.6 mg). 1 H NMR (400 MHz, CDCl 3 ): δ 7.90 (d, J = 8.5 Hz, 2H), 7.25 (d, J = 6.7 Hz, 1H), 6.72 (d, J = 8.5 Hz, 2H), 3.95 (br s, 2H), 2.70 (s, 3H), 2.48 (s, 3H). 13 C NMR (100 MHz, CDCl 3 ): δ 167.6, 166.5, 163.7, 149.0, 128.6, 126.9, 114.8, 111.8, 26.2, HRMS (EI) m/z: [M] + calcd for C 12 H 13 N 3 : found, ,6-dichloro-4-(2,6-dimethylpyrimidin-4-yl)aniline (3l) S7
8 silica gel to afford a yellow solid in 84% yield (67.5 mg). mp ºC ; 1 H NMR (400 MHz, CDCl 3 ): δ 7.94 (s, 2H), 7.19 (s, 1H), 4.73 (br s, 2H), 2.70 (s, 3H), 2.50 (s, 3H). 13 C NMR (100 MHz, CDCl 3 ): δ 167.8, 167.2, 161.4, 142.0, 127.1, 126.6, 119.6, 111.8, 26.1, HRMS (EI) m/z: [M] + calcd for C 12 H 11 Cl 2 N 3 : found, (2,6-dimethylpyrimidin-4-yl)phenol (3m) silica gel to afford a yellow solid in 57% yield (34.2 mg). mp ºC ; 1 H NMR (400 MHz, CDCl 3 ): δ (brs, 1H), 7.77 (d, J = 8.0 Hz, 1H), 7.47 (s, 1H), (m, 1H), 7.01 (d, J = 8.3 Hz, 1H), 6.90 (t, J = 7.6 Hz, 1H), 2.72 (s, 3H), 2.56 (s, 3H). 13 C NMR (100 MHz, CDCl 3 ): δ 168.0, 165.2, 164.1, 161.2, 133.2, 126.7, 119.0, 118.8, 116.7, 111.1, 25.6, HRMS (EI) m/z: [M] + calcd for C 12 H 12 N 2 O: found, ,4-dimethyl-6-(naphthalen-2-yl)pyrimidine (3n) silica gel to afford a yellow solid in 75% yield (52.6 mg). mp ºC; 1 H NMR (400 MHz, CDCl 3 ): δ 8.58 (s, 1H), 8.14 (d, J = 8.5 Hz, 1H), 7.95 (t, J = 8.0 Hz, 2H), (m, 1H), (m, 3H), 2.81 (s, 3H), 2.58 (s, 3H). 13 C NMR (100 MHz, CDCl 3 ): δ 168.0, 167.3, 163.8, 134.4, 133.3, 128.9, 128.6, 127.7, 127.3, 127.2, 126.5, 124.1, 113.6, 26.3, HRMS (EI) m/z: [M] + calcd for C 16 H 14 N 2 : found, S8
9 4-(9H-fluoren-2-yl)-2,6-dimethylpyrimidine (3o) silica gel to afford a yellow solid in 52% yield (42.4 mg). mp ºC; 1 H NMR (400 MHz, CDCl 3 ): δ 8.28 (s, 1H), 8.06 (d, J = 7.9 Hz, 1H), 7.85 (dd, J = 12.8, 7.7 Hz, 2H), 7.58 (d, J = 7.3 Hz, 1H), 7.42 (s, 1H), 7.40 (d, J = 7.3 Hz, 1H), 7.35 (t, J = 7.0 Hz, 1H), 3.98 (s, 2H), 2.78 (s, 3H), 2.56 (s, 3H). 13 C NMR (100 MHz, CDCl 3 ): δ 167.8, 167.1, 164.1, 144.2, 144.0, 143.9, 140.9, 135.5, 127.4, 126.9, 126.1, 125.2, 123.8, 120.4, 120.1, 113.3, 36.9, 26.2, HRMS (EI) m/z: [M] + calcd for C 19 H 16 N 2 : found, ,4-dimethyl-6-(thiophen-2-yl)pyrimidine (3p) 2 silica gel to afford a white solid in 77% yield (43.9 mg). mp ºC; 1 H NMR (400 MHz, CDCl 3 ): δ 7.72 (d, J = 3.7 Hz, 1H), 7.47 (d, J = 5.0 Hz, 1H), 7.22 (s, 1H), (m, 1H), 2.68 (s, 3H), 2.49 (s, 3H). 13 C NMR (100 MHz, CDCl 3 ): δ 167.9, 167.0, 158.7, 142.5, 129.5, 128.2, 126.9, 111.4, 26.0, ,4-dimethyl-6-(pyridin-3-yl)pyrimidine (3q) 3 silica gel to afford a yellow oil in 75% yield (41.6 mg). 1 H NMR (400 MHz, CDCl 3 ): δ 9.23 (s, 1H), 8.72 (s, 1H), 8.38 (d, J = 7.9 Hz, 1H), (m, 1H), 7.39 (s, 1H), 2.76 (s, 3H), 2.57 (s, 3H). 13 C NMR (100 MHz, CDCl 3 ): δ 168.3, 167.8, 161.5, 151.3, 148.4, 134.7, 132.7, 113.5, 26.1, ,4-dimethyl-6-phenethylpyrimidine (3r) 4 S9
10 silica gel to afford a yellow oil in 71% yield (45.2 mg). 1 H NMR (400 MHz, CDCl 3 ): δ (m, 2H), (m, 3H), 6.76 (s, 1H), (m, 4H), 2.69 (s, 3H), 2.42 (s, 3H). 13 C NMR (100 MHz, CDCl 3 ): δ 169.2, 167.5, 166.6, 140.9, 128.4, 128.3, 126.1, 116.7, 39.4, 35.0, 26.0, cyclohexyl-2,6-dimethylpyrimidine (3s) 5 silica gel to afford a yellow oil in 51% yield (29.1 mg). 1 H NMR (400 MHz, CDCl 3 ): δ 6.81 (s, 1H), 2.65 (s, 3H), (m, 1H), 2.44 (s, 3H), (m, 2H), (m, 2H), (m, 1H), (m, 5H). 13 C NMR (100 MHz, CDCl 3 ): δ 174.4, 167.1, 166.6, 114.4, 46.0, 32.2, 26.3, 26.0, 25.9, ((3r,5r,7r)-adamantan-1-yl)-2,6-dimethylpyrimidine (3t) silica gel to afford a white solid in 47% yield (34.1 mg). mp ºC; 1 H NMR (400 MHz, CDCl 3 ): δ 6.88 (s, 1H), 2.65 (s, 3H), 2.44 (s, 3H), 2.09 (s, 3H), 1.93 (s, 6H), 1.77 (s, 6H). 13 C NMR (100 MHz, CDCl 3 ): δ 177.0, 166.9, 166.4, 112.6, 41.1, 38.7, 36.7, 28.5, 26.2, HRMS (EI) m/z: [M] + calcd for C 16 H 22 N 2 : found, ,4-dibutyl-6-phenylpyrimidine (3u) S10
11 silica gel to afford a yellow oil in 74% yield (59.5 mg). 1 H NMR (400 MHz, CDCl 3 ): δ 8.07 (d, J = 7.6 Hz, 2H), 7.48 (d, J = 5.1 Hz, 3H), 7.34 (s, 1H), (m, 2H), (m, 2H), (m, 2H), (m, 2H), (m, 4H), (m, 6H). 13 C NMR (100 MHz, CDCl 3 ): δ 171.4, 171.3, 163.8, 137.6, 130.4, 128.8, 127.2, 112.7, 39.5, 38.0, 31.3, 31.0, 22.6, 22.5, 14.0, HRMS (EI) m/z: [M] + calcd for C 18 H 24 N 2 : found, ,4-dibutyl-6-(4-fluorophenyl)pyrimidine (3v) silica gel to afford a yellow oil in 81% yield (69.5 mg). 1 H NMR (400 MHz, CDCl 3 ): δ 8.07 (dd, J = 8.1, 5.8 Hz, 2H), 7.29 (s, 1H), 7.15 (t, J = 8.5 Hz, 2H), (m, 2H), (m, 2H), (m, 2H), (m, 2H), (m, 4H), (m, 6H). 13 C NMR (100 MHz, CDCl 3 ): δ 171.3, (d, J = Hz), 162.6, (d, J = 3.0 Hz), (d, J = 8.6 Hz), (d, J = 21.7 Hz), 112.3, 39.4, 37.9, 31.3, 31.0, 22.6, 22.5, 14.0, HRMS (EI) m/z: [M] + calcd for C 18 H 23 FN 2 : found, ,4-dibutyl-6-(p-tolyl)pyrimidine (3w) silica gel to afford a yellow oil in 65% yield (55.0 mg). 1 H NMR (400 MHz, CDCl 3 ): δ 7.97 (d, J = 8.1 Hz, 2H), 7.31 (s, 1H), 7.28 (d, J = 8.0 Hz, 2H), (m, 2H), (m, 2H), 2.41 (s, 3H), (m, 2H), (m, 2H), (m, 4H), (m, 6H). 13 C NMR (100 MHz, CDCl 3 ): δ 171.2, 171.0, 163.7, 140.7, 134.7, 129.5, 127.1, 112.4, 39.5, 38.0, 31.4, 31.1, 22.7, 22.5, 21.4, 14.0, HRMS (EI) m/z: [M] + calcd S11
12 for C 19 H 26 N 2 : found, ,4,6-triphenylpyrimidine (3x) 6 silica gel to afford a white solid in 78% yield (72.1 mg). mp ºC; 1 H NMR (400 MHz, CDCl 3 ): δ 8.75 (m, 2H), 8.30 (m, 4H), 8.02 (s, 1H), (m, 9H). 13 C NMR (100 MHz, CDCl 3 ): δ 164.7, 164.5, 138.1, 137.5, 130.7, 130.6, 128.9, 128.5, 128.4, 127.3, (4-fluorophenyl)-2,6-diphenylpyrimidine (3y) 6 silica gel to afford a white solid in 90% yield (88.0 mg). mp ºC; 1 H NMR (400 MHz, CDCl 3 ): δ 8.75 (d, J = 7.1 Hz, 2H), (m, 4H), 8.00 (s, 1H), (m, 6H), 7.28 (d, J = 5.2 Hz, 2H). 13 C NMR (100 MHz, CDCl 3 ): δ 164.8, (d, J = Hz), 164.4, 163.5, 138.0, 137.4, (d, J = 2.9 Hz), 130.8, 130.7, (d, J = 8.7 Hz), 128.9, 128.5, 128.4, 127.3, (d, J = 21.7 Hz), ,4-diphenyl-6-(p-tolyl)pyrimidine (3za) 6 silica gel to afford a white solid in 70% yield (67.6 mg). mp ºC; 1 H NMR (400 MHz, CDCl 3 ): δ 8.74 (d, J = 7.2 Hz, 2H), 8.29 (d, J = 6.8 Hz, 2H), 8.20 (d, J = 7.9 Hz, 2H), 7.99 (s, 1H), (m, 6H), 7.36 (d, J = 7.8 Hz, 2H), 2.46 (s, 3H). 13 C NMR (100 MHz, CDCl 3 ): δ 164.6, 164.5, 164.4, 141.1, 138.2, 137.6, 134.7, 130.6, 130.5, 129.6, 128.9, 128.5, 128.4, 127.2, 127.1, 109.9, (4-fluorophenyl)-2,6-di-p-tolylpyrimidine (3zb) S12
13 silica gel to afford a white solid in 87% yield (92.4 mg). mp ºC; 1 H NMR (400 MHz, CDCl 3 ): δ 8.60 (d, J = 7.4 Hz, 2H), (m, 2H), 8.18 (d, J = 7.4 Hz, 2H), 7.89 (s, 1H), 7.35 (t, J = 6.6 Hz, 4H), 7.23 (t, J = 8.9 Hz, 2H), 2.46 (s, 6H). 13 C NMR (100 MHz, CDCl 3 ): δ 164.6, (d, J = Hz), 164.5, 163.3, (d, J = 30.7 Hz), 135.4, 134.7, (d, J = 3.0 Hz), 129.6, 129.3, 129.2, 128.4, 127.1, (d, J = 21.7 Hz), 109.2, 21.5, HRMS (EI) m/z: [M] + calcd for C 24 H 19 FN 2 : found, (4-fluorophenyl)-2,6-di-m-tolylpyrimidine (3zc) silica gel to afford a white solid in 93% yield (98.7 mg). mp ºC; 1 H NMR (400 MHz, CDCl 3 ): δ 8.51 (d, J = 6.6 Hz, 2H), (m, 2H), 8.05 (d, J = 9.3 Hz, 2H), 7.91 (s, 1H), 7.44 (dd, J = 11.2, 7.4 Hz, 2H), 7.35 (t, J = 6.9 Hz, 2H), 7.24 (t, J = 7.9 Hz, 2H), 2.51 (s, 6H). 13 C NMR (100 MHz, CDCl 3 ): δ 164.9, 164.6, (d, J = Hz), 163.4, 138.6, (d, J = 3.0 Hz), 137.4, (d, J = 3.1 Hz), (d, J = 10.2 Hz), 129.3, 129.2, 128.9, 128.8, 128.3, 127.8, 125.7, 124.4, (d, J = 21.7 Hz), 109.9, 21.6, HRMS (EI) m/z: [M] + calcd for C 24 H 19 FN 2 : found, (4-fluorophenyl)-2,6-di(thiophen-3-yl)pyrimidine (3zd) S13
14 silica gel to afford a white solid in 92% yield (93.3 mg). mp ºC; 1 H NMR (400 MHz, CDCl 3 ): δ 8.43 (s, 1H), (m, 3H), 8.06 (d, J = 4.9 Hz, 1H), 7.81 (d, J = 4.9 Hz, 1H), 7.68 (s, 1H), (m, 1H), (m, 1H), 7.21 (t, J = 8.0 Hz, 2H). 13 C NMR (100 MHz, CDCl 3 ): δ 163.5, 163.3, (d, J = Hz), 161.8, 142.1, 140.5, (d, J = 2.9 Hz), (d, J = 8.6 Hz), 127.9, 127.7, 126.7, 126.6, 126.1, 125.7, (d, J = 21.7 Hz), HRMS (EI) m/z: [M] + calcd for C 18 H 11 FN 2 S 2 : found, butyl-4-methyl-6-phenylpyrimidine (3ze) silica gel to afford a yellow oil in 73% yield (49.5 mg). 1 H NMR (400 MHz, CDCl 3 ): δ (m, 2H), 7.47 (s, 3H), 7.36 (s, 1H), 2.97 (t, J = 7.6 Hz, 2H), 2.55 (s, 3H), (m, 2H), (m, 2H), 0.96 (t, J = 7.2 Hz, 3H). 13 C NMR (100 MHz, CDCl 3 ): δ 171.4, 167.2, 163.8, 137.4, 130.5, 128.9, 127.2, 113.5, 39.5, 31.1, 24.4, 22.7, HRMS (EI) m/z: [M] + calcd for C 15 H 18 N 2 : found, heptyl-4-methyl-6-phenylpyrimidine (3zf) silica gel to afford a yellow oil in 66% yield (53.1 mg). 1 H NMR (400 MHz, CDCl 3 ): δ (m, 2H), 7.48 (s, 3H), 7.36 (s, 1H), 2.96 (t, J = 7.4 Hz, 2H), 2.55 (s, 3H), (m, 2H), (m, 4H), 1.28 (s, 4H), 0.87 (t, J = 7.2 Hz, 3H). 13 C NMR (100 MHz, CDCl 3 ): δ 171.3, 167.2, 163.8, 137.4, 130.5, 128.8, 127.2, 113.5, 39.8, 31.8, 29.5, 29.2, 28.9, 24.4, 22.6, HRMS (EI) m/z: [M] + calcd for C 18 H 24 N 2 : found, S14
15 4-methyl-6-phenyl-2-(3-phenylpropyl)pyrimidine (3zg) silica gel to afford a yellow oil in 70% yield (60.5 mg). 1 H NMR (400 MHz, CDCl 3 ): δ (m, 2H), 7.49 (s, 3H), 7.38 (s, 1H), (m, 4H), 7.19 (d, J = 6.7 Hz, 1H), 3.05 (t, J = 7.4 Hz, 2H), 2.77 (t, J = 7.2 Hz, 2H), 2.56 (s, 3H), (m, 2H). 13 C NMR (100 MHz, CDCl 3 ): δ 170.7, 167.2, 163.7, 142.3, 137.2, 130.5, 128.8, 128.5, 128.2, 127.1, 125.7, 113.5, 39.2, 35.7, 30.4, HRMS (EI) m/z: [M] + calcd for C 20 H 20 N 2 : found, methyl-6-phenyl-2-(p-tolyl)pyrimidine (3zh) silica gel to afford a yellow solid in 80% yield (62.4 mg). mp ºC ; 1 H NMR (400 MHz, CDCl 3 ): δ 8.49 (d, J = 7.6 Hz, 2H), 8.21 (d, J = 5.8 Hz, 2H), 7.51 (s, 3H), 7.44 (s, 1H), 7.31 (d, J = 7.6 Hz, 2H), 2.64 (s, 3H), 2.44 (s, 3H). 13 C NMR (100 MHz, CDCl 3 ): δ 167.6, 164.3, 163.5, 140.6, 137.3, 135.4, 130.5, 129.2, 128.8, 128.2, 127.1, 113.7, 24.6, HRMS (EI) m/z: [M] + calcd for C 18 H 16 N 2 : found, methyl-6-phenyl-2-(m-tolyl)pyrimidine (3zi) silica gel to afford a yellow solid in 81% yield (63.2 mg). mp ºC ; 1 H NMR (400 MHz, CDCl 3 ): δ 8.41 (s, S15
16 2H), 8.21 (d, J = 5.7 Hz, 2H), 7.52 (s, 3H), 7.46 (s, 1H), 7.41 (t, J = 6.8 Hz, 1H), 7.31 (d, J = 7.2 Hz, 1H), 2.65 (s, 3H), 2.49 (s, 3H). 13 C NMR (100 MHz, CDCl 3 ): δ 167.6, 164.4, 163.6, 138.0, 137.2, 131.2, 130.6, 128.8, 128.3, 127.1, 125.5, 113.9, 24.6, HRMS (EI) m/z: [M] + calcd for C 18 H 16 N 2 : found, methyl-6-phenyl-2-(o-tolyl)pyrimidine (3zj) silica gel to afford a yellow oil in 78% yield (60.8 mg). 1 H NMR (400 MHz, CDCl 3 ): δ (m, 2H), 7.88 (d, J = 6.7 Hz, 1H), 7.50 (s, 4H), 7.32 (d, J = 6.3 Hz, 3H), 2.66 (s, 3H), 2.63 (s, 3H). 13 C NMR (100 MHz, CDCl 3 ): δ 167.5, 167.4, 163.4, 138.6, 137.2, 131.2, 130.6, 130.4, 129.2, 128.8, 127.2, 125.9, 113.4, 24.6, HRMS (EI) m/z: [M] + calcd for C 18 H 16 N 2 : found, (4-fluorophenyl)-4-methyl-6-phenylpyrimidine (3zk) silica gel to afford a white solid in 84% yield (66.5 mg). mp ºC ; 1 H NMR (400 MHz, CDCl 3 ): δ 8.59 (t, J = 6.5 Hz, 2H), (m, 2H), 7.52 (s, 3H), 7.45 (s, 1H), 7.17 (t, J = 8.2 Hz, 2H), 2.63 (s, 3H). 13 C NMR (100 MHz, CDCl 3 ): δ 167.8, (d, J = Hz), 163.7, 163.3, 137.1, (d, J = 2.8 Hz), 130.7, (d, J = 8.6 Hz), 128.8, 127.1, (d, J = 21.6 Hz), 113.8, HRMS (EI) m/z: [M] + calcd for C 17 H 13 FN 2 : found, methyl-6-phenylpyrimidin-2-amine (3zl) S16
17 silica gel to afford a white solid in 90% yield (49.9 mg). mp ºC ; 1 H NMR (400 MHz, CDCl 3 ): δ (m, 2H), (m, 3H), 6.90 (s, 1H), 5.34 (br s, 2H), 2.40 (s, 3H). 13 C NMR (100 MHz, CDCl 3 ): δ 168.5, 165.3, 163.2, 137.5, 130.3, 128.6, 127.0, 107.3, HRMS (EI) m/z: [M] + calcd for C 11 H 11 N 3 : found, methyl-6-phenyl-2-(thiophen-3-yl)pyrimidine (3zm) silica gel to afford a yellow oil in 76% yield (57.5 mg). 1 H NMR (400 MHz, CDCl 3 ): δ 8.39 (s, 1H), (m, 2H), (m, 1H), 7.51 (s, 3H), 7.39 (d, J = 6.7 Hz, 2H), 2.61 (s, 3H). 13 C NMR (100 MHz, CDCl 3 ): δ 167.7, 163.6, 161.5, 142.1, 137.1, 130.6, 128.8, 127.7, 127.1, 125.7, 113.5, HRMS (EI) m/z: [M] + calcd for C 15 H 12 N 2 S: found, ,6-dimethyl-2-(m-tolyl)pyrimidine (3zn) silica gel to afford a yellow oil in 92% yield (54.6 mg). 1 H NMR (400 MHz, CDCl 3 ): δ 8.22 (d, J = 9.9 Hz, 2H), 7.36 (t, J = 7.5 Hz, 1H), 7.27 (d, J = 7.2 Hz, 1H), 6.92 (s, 1H), 2.53 (s, 6H), 2.44 (s, 3H). 13 C NMR (100 MHz, CDCl 3 ): δ 166.7, 164.3, 138.0, 131.1, 128.7, 128.4, 125.4, 117.9, 24.2, HRMS (EI) m/z: [M] + calcd for C 13 H 14 N 2 : found, methyl-6-phenylpyrimidine-4-carbaldehyde (4) S17
18 silica gel to afford a white solid in 72% yield (31.1 mg). mp ºC; 1 H NMR (400 MHz, CDCl 3 ): δ 10.0 (s, 1H), (m, 2H), 7.96 (s, 1H), 7.19 (t, J = 8.2 Hz, 2H), 2.87 (s, 3H). 13 C NMR (100 MHz, CDCl 3 ): δ 193.3, 169.7, 165.1, (d, J = Hz), 158.7, 132.3, (d, J = 8.8 Hz), (d, J = 21.9 Hz), 109.2, HRMS (EI) m/z: [M] + calcd for C 12 H 9 FN 2 O: found, (Z)-3-amino-1-phenylbut-2-en-1-one (6a) 7 silica gel to afford a white solid. 1 H NMR (400 MHz, CDCl 3 ): δ (br s, 1H), 7.86 (d, J = 7.3 Hz, 2H), (m, 3H), 5.71 (s, 1H), 5.44 (br s, 1H), 2.03 (s, 3H). 13 C NMR (100 MHz, CDCl 3 ): δ 189.4, 163.2, 140.1, 130.7, 128.1, 127.0, 92.2, References (1) Bagley, M. C.; Hughes, D. D.; Lubinu, M. C.; Merritt, E. A.; Taylor, P. H.; Tomkinson, N. C. O. QSAR Comb. Sci. 2004, 23, 859. (2) Kondo, Y.; Watanabe, R.; Sakamoto, T.; Yamanaka, H. Chem. Pharm. Bull. 1989, 37, (3) Sakamoto, T.; Kondo, Y.; Murata, N.; Yamanaka, H. Tetrahedron 1993, 49, (4) Edo, K.; Sakamoto, T.; Yamanaka, H. Chem. Pharm. Bull. 1978, 26, (5) Gøgsig, T. M.; Lindhardt, A. T.; Skrydstrup, T. Org. Lett. 2009, 11, (6) Vadagaonkar, K. S.; Kalmode, H. P.; Prakashb, S.; Chaskar, A. C. New J. Chem. 2015, 39, (7) Xu, S.-L.; Li, C.-P.; Li, J.-H.; Synlett 2009, 5, 818. S18
19 5. Copies of 1 H and 13 C NMR Spectra of the Products 1 H NMR Spectrum of 3a 13 C NMR Spectrum of 3a S19
20 1 H NMR Spectrum of 3b 13 C NMR Spectrum of 3b S20
21 1 H NMR Spectrum of 3c 13 C NMR Spectrum of 3c S21
22 1 H NMR Spectrum of 3d 13 C NMR Spectrum of 3d S22
23 1 H NMR Spectrum of 3e 13 C NMR Spectrum of 3e S23
24 1 H NMR Spectrum of 3f 13 C NMR Spectrum of 3f S24
25 1 H NMR Spectrum of 3g 13 CNMR Spectrum of 3g S25
26 1 H NMR Spectrum of 3h 13 C NMR Spectrum of 3h S26
27 1 H NMR Spectrum of 3i 13 C NMR Spectrum of 3i S27
28 1 H NMR Spectrum of 3j 13 C NMR Spectrum of 3j S28
29 1 H NMR Spectrum of 3k 13 C NMR Spectrum of 3k S29
30 1 H NMR Spectrum of 3l 13 C NMR Spectrum of 3l S30
31 1 H NMR Spectrum of 3m 13 C NMR Spectrum of 3m S31
32 1 H NMR Spectrum of 3n 13 C NMR Spectrum of 3n S32
33 1 H NMR Spectrum of 3o 13 C NMR Spectrum of 3o S33
34 1 H NMR Spectrum of 3p 13 C NMR Spectrum of 3p S34
35 1 H NMR Spectrum of 3q 13 C NMR Spectrum of 3q S35
36 1 H NMR Spectrum of 3r 13 C NMR Spectrum of 3r S36
37 1 H NMR Spectrum of 3s 13 C NMR Spectrum of 3s S37
38 1 H NMR Spectrum of 3t 13 C NMR Spectrum of 3t S38
39 1 H NMR Spectrum of 3u 13 C NMR Spectrum of 3u S39
40 1 H NMR Spectrum of 3v 13 C NMR Spectrum of 3v S40
41 1 H NMR Spectrum of 3w 13 C NMR Spectrum of 3w S41
42 1 H NMR Spectrum of 3x 13 C NMR Spectrum of 3x S42
43 1 H NMR Spectrum of 3y 13 C NMR Spectrum of 3y S43
44 1 H NMR Spectrum of 3za 13 C NMR Spectrum of 3za S44
45 1 H NMR Spectrum of 3zb 13 C NMR Spectrum of 3zb S45
46 1 H NMR Spectrum of 3zc 13 C NMR Spectrum of 3zc S46
47 1 H NMR Spectrum of 3zd 13 C NMR Spectrum of 3zd S47
48 1 H NMR Spectrum of 3ze 13 C NMR Spectrum of 3ze S48
49 1 H NMR Spectrum of 3zf 13 C NMR Spectrum of 3zf S49
50 1 H NMR Spectrum of 3zg 13 C NMR Spectrum of 3zg S50
51 1 H NMR Spectrum of 3zh 13 C NMR Spectrum of 3zh S51
52 1 H NMR Spectrum of 3zi 13 C NMR Spectrum of 3zi S52
53 1 H NMR Spectrum of 3zj 13 C NMR Spectrum of 3zj S53
54 1 H NMR Spectrum of 3zk 13 C NMR Spectrum of 3zk S54
55 1 H NMR Spectrum of 3zl 13 C NMR Spectrum of 3zl S55
56 1 H NMR Spectrum of 3zm 13 C NMR Spectrum of 3zm S56
57 1 H NMR Spectrum of 3zn 13 C NMR Spectrum of 3zn S57
58 1 H NMR Spectrum of 4 13 C NMR Spectrum of 4 S58
59 1 H NMR Spectrum of 6a 13 C NMR Spectrum of 6a S59
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