(Pyrimidin-5-yl)boronic acid → 5-((6-Phenylpyridin-3-yl)methyl)pyrimidine

Participants

Reaction Steps

Synthesized using compound 61a (219 mg, 0.88 mmol) and pyrimidine-5-boronic acid (164 mg, 1.32 mmol) according to Method C. Crude product was purified by flash chromatography on silica-gel using a mixture of hexane/ethyl acetate (1:1) 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. White solid. Yield: 43 mg, 20%. 1H NMR (CDCl3, 500 MHz): δH (ppm)=4.02 (s, 2H), 7.39-7.44 (m, 1H), 7.44-7.56 (m, 3H), 7.70 (dd, J=8.2, 0.9 Hz, 1H), 7.95-8.00 (m, 2H), 8.58-8.67 (m, 3H), 9.13 (s, 1H); 13C NMR (CDCl3, 125 MHz): δC (ppm)=33.4, 120.5, 126.8, 128.8, 129.1, 132.2, 133.3, 136.9, 138.7, 149.7, 156.4, 156.9, 157.3; (ESI): m/z=247.83 [M+H]+.

Provenance & Evidence