3-Pyridinylboronic acid → 2-Phenyl-5-(pyridin-3-ylmethyl)pyrimidine
Reaction equation
Br[CH2:2][C:3]1[CH:4]=[N:5][C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[N:7][CH:8]=1.[N:15]1[CH:20]=[CH:19][CH:18]=[C:17](B(O)O)[CH:16]=1>>[C:9]1([C:6]2[N:5]=[CH:4][C:3]([CH2:2][C:17]3[CH:16]=[N:15][CH:20]=[CH:19][CH:18]=3)=[CH:8][N:7]=2)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1Participants
3
Procedure
Synthesized using compound 64a (100 mg, 0.41 mmol) and pyridine-3-boronic acid (74 mg, 0.60 mmol) according to Method C. Crude product was purified by flash chromatography on silica-gel using a mixture of hexane/ethyl acetate (1:2) as eluent. After flash chromatography the product was solved in ethyl acetate and a few drops of conc. HCl and water were added. After stirring for 30 minutes the phases were separated and water phase was neutralized with aqueous Na2CO3-solution (2M). After extraction with ethyl acetate and drying over MgSO4 the solvent was removed under vacuum. Light orange solid. Yield: 72 mg, 71%. 1H NMR (CDCl3, 500 MHz): δH (ppm)=3.76 (s, 2H), 7.00-7.05 (m, 1H), 7.23-7.29 (m, 4H), 8.16-8.22 (m, 2H), 8.27-8.36 (m, 2H), 8.40-8.43 (m, 2H); 13C NMR (CDCl3, 125 MHz): δC (ppm)=33.5, 123.7, 128.0, 128.6, 130.5, 130.7, 134.2, 136.1, 137.2, 148.4, 150.0, 157.3, 163.3; (ESI): m/z=247.92 [M+H]+.