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

Temperature

100 °C

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.

1. customThe tubes were sealed
2. temperatureAfter cooling
3. customthe combined mixtures were partitioned between brine/water (1:1, 900 ml) and ethyl acetate (225 ml)
4. filtrationThe mixture was filtered through a plug of Celite
5. customThe aqueous phase was separated
6. extractionextracted with ethyl acetate (3×225 ml)
7. washThe combined organic layers were washed with brine/water (1:1, 4×225 ml)
8. dry with materialdried (anhydrous sodium sulfate)
9. filtrationfiltered
10. customThe resulting residue was purified by silica gel chromatography (gradient 0-20% ethyl acetate in cyclohexane)

ORD record

ord-d809a19d82294ae8b51946e7de5a1e7a

Source dataset

uspto-grants-2015_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09156853B2