Bromine → 6-Bromo-3-(2,2,2-trifluoroethyl)furo[2,3-d]pyrimidin-4(3H)-one

To a stirred solution of 3-(2,2,2-trifluoroethyl)furo[2,3-d]pyrimidin-4(3H)-one (0.64 g, 2.93 mmol) in anhydrous DMF (11 ml) at 0° C. was added bromine (0.333 ml, 6.45 mmol) and the mixture stirred for 30 min. The mixture was partitioned between ethyl acetate (30 ml) and an aqueous mixture (3:1:4, water, saturated sodium hydrogen carbonate solution and 20% w/w sodium thiosulfate solution, 110 ml). The aqueous phase was separated and extracted with ethyl acetate (3×30 ml). The combined ethyl acetate fractions were washed with brine/water (1:1, 4×30 ml), dried (anhydrous sodium sulfate), filtered and reduced in vacuo. The resulting residue was purified by silica gel chromatography (gradient 0-30% ethyl acetate in cyclohexane) to afford the title compound (673 mg, 77%). LCMS RT=1.04 min, [M+H+(79Br)]=297.0, [M+H+(81Br)]=298.9.

1. customThe mixture was partitioned between ethyl acetate (30 ml)
2. customThe aqueous phase was separated
3. extractionextracted with ethyl acetate (3×30 ml)
4. washThe combined ethyl acetate fractions were washed with brine/water (1:1, 4×30 ml)
5. dry with materialdried (anhydrous sodium sulfate)
6. filtrationfiltered
7. customThe resulting residue was purified by silica gel chromatography (gradient 0-30% ethyl acetate in cyclohexane)

ORD record

ord-58e5c9b979a94decb77609171a0f842c

Source dataset

uspto-grants-2015_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09156853B2