2,2,2-Trifluoroethanol → HCID 18753241, compound

Participants

Reaction Steps

A solution of 56 mg (0.55 mmol) of 2,2,2-trifluoroethanol in 5 ml of tetrahydrofurane was cooled to 0° C. and treated under an argon atmosphere with 23 mg (0.52 mmol) of sodium hydride (55% dispersion in oil). The mixture was kept at 0° C. during 10 min, then a solution of 200 mg (0.58 mmol) of 4-chloro-2-methylsulfanyl-6-(4-phenyl-piperidin-1-yl)-pyrimidine-5-carbonitrile in 5 ml of tetrahydrofurane was added and, thereupon, the mixture was warmed to room temperature and stirring continued during 36 hours. For the working-up, the reaction mixture was evaporated and the residue obtained was directly chromatographed on silica gel using a 9:1 mixture of hexane and ethyl acetate as the eluent yielding 142 mg (0.35 mmol, 60% of theory) of the 2-methylsulfanyl-4-(4-phenyl-piperidin-1-yl)-6-(2,2,2-trifluoro-ethoxy)-pyrimidine-5-carbonitrile as an amorphous, white solid; MS: [M+H]+=409.

Provenance & Evidence