Dimethyl Sulfoxide → HCID 14513901, compound

Participants

Reaction Conditions

Reaction Steps

Dimethylsulfoxide (DMSO) (3.10 gm, 39.7 mmol) was added to a solution of oxalyl chloride (2.520 gm, 19.8 mmol) in methylene chloride (100 ml) which was cooled to -78° C. under argon. The solution was allowed to stir 15 minutes. Then, 4-(4-fluorophenyl)-6-(1-methylethyl)-2-phenyl-5-hydroxymethylene-pyrimidine obtained in step (iii) above (4.942 gm, 15.3 mmol) was added to the flask as a methylene chloride/THF (25 ml/10 ml) solution. The solution was stirred for 20 minutes and then triethylamine (10.6 ml) was added. The solution was stirred for an additional 10 minutes, then was warmed to room temperature. The solution was diluted with ether, washed with water and brine, then dried over Na2SO4, filtered and concentrated to afford a yellow solid. The solid was recrystallized from EtOAc/hexane to give the title compound as fine yellow needles (4.064 gm, 83%) (mp: 127-129° C.).

Provenance & Evidence