Sodium Methoxide → HCID 68752347, compound

Participants

Reaction Steps

To a solution of rac-5-[(4S*,5R*)-4,5-bis-(4-chloro-phenyl)-4,5-dimethyl-4,5-dihydro-1H-imidazol-2-yl]-4-ethoxy-2-methylsulfanyl-pyrimidine (250 mg, 0.513 mmol) in methanol (10 mL) was added sodium methoxide (4.1 mL, 0.5M solution in methanol, Aldrich). The mixture was stirred at room temperature overnight then concentrated under reduced pressure. The crude residue was taken in ethyl acetate and washed with water and brine. The organic layer was dried over anhydrous sodium sulfate, filtered and concentrate under reduced pressure to give rac-5-[(4S*,5R*)-4,5-bis-(4-chloro-phenyl)-4,5-dimethyl-4,5-dihydro-1H-imidazol-2-yl]-2,4-dimethoxy-pyrimidine (˜200 mg). It was then taken in ethanol (15 mL) and sodium ethoxide (58.1 mg, Fluka) was added. The reaction mixture was left in the fridge overnight then concentrated under reduced pressure. The crude residue was taken in ethyl acetate and washed with water and brine. The organic layer was dried over anhydrous sodium sulfate, filtered and concentrate under reduced pressure. Purification of the crude residue by flash column chromatography (12 g of silica gel, eluting with 20-100% ethyl acetate in hexanes then with 3% methanol in ethyl acetate) gave rac-5-[(4S*,5R*)-4,5-bis-(4-chloro-phenyl)-4,5-dimethyl-4,5-dihydro-1H-imidazol-2-yl]-2,4-diethoxy-pyrimidine as an off-white foam (132 mg, 62%). HR-MS (ES, m/z) calculated for C25H27N4O2Cl2 [(M+H)+] 485.1506, observed 485.1508.

Provenance & Evidence