Dimethyl Sulfoxide → HCID 131734588, compound

Participants

Reaction Steps

Oxalyl chloride (0.21 mL, 2.39 mmol) was added to a solution of dimethyl sulfoxide (0.34 mL, 4.78 mmol) in methylene chloride (20 mL) at −78° C. The mixture was stirred for 10 minutes and 1-((tert-butyldimethylsilyl)oxy)-3-(4-(3-((4-(difluoromethyl)pyrimidin-2-yl)amino)-5-methylphenyl)-1H-pyrazol-1-yl)propan-2-ol (780 mg, 1.59 mmol) was added. After stirring for additional 15 minutes, triethylamine (1.11 mL, 7.97 mmol) was added. The mixture was allowed to warm to room temperature for 2 h. Water was added to the mixture, which was then extracted with methylene chloride. The organic layer was dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (0-40% EtOAc/Hexane) to afford 1-((tert-butyldimethylsilyl)oxy)-3-(4-(3-((4-(difluoromethyl)pyrimidin-2-yl)amino)-5-methylphenyl)-1H-pyrazol-1-yl)propan-2-one. MS ESI calc'd. for C24H32F2N5O2Si [M+H]+ 488. found 488.

Provenance & Evidence