Dimethylformamide → 3-(2,2,2-Trifluoroethyl)furo[2,3-d]pyrimidin-4(3H)-one

Participants

Reaction Conditions

Reaction Steps

Into seven 20 ml microwave tubes were placed 2-iodo-N-(2,2,2-trifluoroethyl)furan-3-carboxamide (0.62 g, 1.94 mmol), formimidamide, HCl (0.78 g, 9.72 mmol), copper(I) iodide (0.037 g, 0.194 mmol) and potassium carbonate (0.81 g, 5.83 mmol) in anhydrous DMF (13 ml). The tubes were sealed and heated to 100° C. for approximately 68 h with stirring. After cooling, the combined mixtures were partitioned between brine/water (1:1, 900 ml) and ethyl acetate (225 ml). The mixture was filtered through a plug of Celite. The aqueous phase was separated and extracted with ethyl acetate (3×225 ml). The combined organic layers were washed with brine/water (1:1, 4×225 ml), dried (anhydrous sodium sulfate), filtered and reduced in vacuo. The resulting residue was purified by silica gel chromatography (gradient 0-20% ethyl acetate in cyclohexane) to afford the title compound (647 mg, 22%). LCMS RT=0.79 min, M+H+=219.1.

Provenance & Evidence