(5S)-5-ethyl-1,3-oxazolidin-2-one → N'-[5-[[4-(cyanomethyl)phenyl]methyl]-4-[(5S)-5-ethyl-2-oxo-1,3-oxazolidin-3-yl]-6-methylpyrimidin-2-yl]-N,N-dimethylmethanimidamide

Participants

Reaction Conditions

Reaction Steps

Palladium(II) acetate (8.22 mg, 0.04 mmol) and 9,9-Dimethyl-4,5-bis(diphenylphosphino)xanthene (42.4 mg, 0.07 mmol) were added to dioxane (3 mL) and the solution was stirred at room temperature for 10 minutes.(E)-N'-(4-chloro-5-(4-(cyanomethyl)benzyl)-6-methylpyrimidin-2-yl)-N,N-dimethylformimidamide (240 mg, 0.73 mmol), (S)-5-ethyloxazolidin-2-one (169 mg, 1.46 mmol) and POTASSIUM CARBONATE (202 mg, 1.46 mmol) were added and the mixture was heated at 100 °C for 1 hour. The solvent was evaporated under reduced pressure and the crude product was purified by flash silica chromatography, elution gradient 2 to 5% methanol in dichloromethane. Pure fractions were evaporated to dryness to afford (S,E)-N'-(5-(4-(cyanomethyl)benzyl)-4-(5-ethyl-2-oxooxazolidin-3-yl)-6-methylpyrimidin-2-yl)-N,N-dimethylformimidamide (136 mg, 45.7 %) as a colorless solid.

Provenance & Evidence