Ammonium formate → 2-Phenyl-5-(2-phenyl-1H-imidazol-5-yl)pyrimidine

Participants

Reaction Conditions

Reaction Steps

To a solution consisting of 5-(1-benzyl-2-phenyl-1H-imidazol-5-yl)-2-phenylpyrimidine (0.495 g, 1.27 mmol) in methanol (100 mL) was added ammonium formate (Aldrich, 0.804 g, 12.7 mmol) and 10% palladium on carbon (Alfa Aesar, 0.500 g). The reaction mixture was brought to reflux at 70° C. for 16 hours. After cooling the solution to room temperature, the crude reaction mixture was filtered over a bed of Celite, which was rinsed with additional methanol (300 mL). Concentration of the filtrate afforded an off-white solid. The product was purified by flash silica column chromatography. Elution through a 40-g Silicycle® flash silica cartridge with gradient of 100% dichloromethane to 5% methanol in dichloromethane afforded the title compound as a white solid (0.218 g, 57% yield); Rf 0.56 with 95:5 v/v dichloromethane-methanol; melting point 253° C.; 1H-NMR (400 MHz; DMSO-d6) δ 9.3 (s, 2H), 8.4 (m, 2H), 8.05 (m, 3H), 7.55-7.35 (m, 6H); MS (ESI+) m/z 299.1 (M+1); H-PGDS FPBA IC50: 0.25 μM; H-PGDS inhibitor EIA IC50: 0.012 μM.

Provenance & Evidence