Phosgene → rac-(4S*,5R*)-2-(2-tert-butyl-4-ethoxy-pyrimidin-5-yl)-4,5-bis-(4-chloro-phenyl)-4,5-dimethyl-4,5-dihydro-imidazole-1-carbonyl chloride

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]-2-tert-butyl-4-ethoxy-pyrimidine (850 mg, 1.71 mmol) and triethylamine (600 uL, 4.28 mmol) in 10 mL of dichloromethane at 0° C. was added 1.88 mL solution of 20% phosgene in toluene (Fluka). After stirring for 30 min the mixture was concentrated to dryness under reduced pressure. Purification by flash column chromatography on silica gel, eluting with 10-20% of ethyl acetate in hexane provided 861 mg of rac-(4S*,5R*)-2-(2-tert-butyl-4-ethoxy-pyrimidin-5-yl)-4,5-bis-(4-chloro-phenyl)-4,5-dimethyl-4,5-dihydro-imidazole-1-carbonyl chloride as an off-white solid.

Provenance & Evidence