(Pyrimidin-5-yl)boronic acid → 2-Phenyl-5-(pyrimidin-5-ylmethyl)pyrimidine

Participants

Reaction Steps

Synthesized using compound 64a (102 mg, 0.41 mmol) and pyrimidine-5-boronic acid (76 mg, 0.61 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. White solid. Yield: 41 mg, 40%. 1H NMR (CDCl3, 500 MHz): δH (ppm)=4.00 (s, 2H), 7.46-7.55 (m, 3H), 8.39-8.47 (m, 2H), 8.63-8.71 (m, 4H), 9.15 (s, 1H); 13C NMR (CDCl3, 125 MHz): δC (ppm)=31.1, 128.1, 128.6, 129.1, 130.9, 132.2, 137.0, 156.9, 157.2, 157.6, 163.7; (ESI): m/z=248.83 [M+H]+.

Provenance & Evidence