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

Participants

Reaction Conditions

Reaction Steps

A mixture of 4′-[(6-ethyl-2,4-dioxo-3,4-dihydrothieno[2,3-d]pyrimidin-1(2H)-yl)methyl]biphenyl-2-carbonitrile (1 g), 2-cyclohexyloxirane (0.98 g), potassium carbonate (0.71 g) and N,N-dimethylformamide (13 mL) was stirred at 80° C. for 20 hr. After allowing to cool to room temperature, ethyl acetate and water were added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was successively washed with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The residue obtained by silica gel column chromatography was dissolved in methylene chloride (8 mL), 4-methylmorpholine-N-oxide (0.34 g), tetrapropylammonium perruthenate (0.026 g) and molecular sieves 4A (0.15 g) were added, and the mixture was stirred at room temperature for 3 hr. The reaction mixture was concentrated under reduced pressure, and silica gel column chromatography gave the title compound as a colorless solid (0.68 g, 52%).

Provenance & Evidence