Dimethyl Sulfoxide → 4'-{[6-ethyl-3-[2-(4-methoxyphenyl)-1-methyl-2-oxoethyl]-2,4-dioxo-3,4-dihydrothieno[2,3-d]pyrimidin-1(2H)-yl]methyl}biphenyl-2-carbonitrile

Participants

Reaction Steps

To a mixture of oxalylchloride (0.12 mL) and methylene chloride (10 mL) were added a solution (5 mL) of dimethyl sulfoxide (0.096 mL) in methylene chloride and a solution (5 mL) of 4′-{[6-ethyl-3-[2-hydroxy-2-(4-methoxyphenyl)-1-methylethyl]-2,4-dioxo-3,4-dihydrothieno[2,3-d]pyrimidin-1(2H)-yl]methyl}biphenyl-2-carbonitrile (0.68 g) in methylene chloride at −78° C., and the mixture was stirred at the same temperature for 15 min. Triethylamine (0.86 mL) was added, and the mixture was allowed to warm to room temperature. The reaction mixture was washed with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography to give the title compound as colorless crystals (0.27 g, 40%).

Provenance & Evidence