Bromine → HCID 117856774, compound

Participants

Reaction Steps

To a stirred solution of 7-methyl-5-(pyridin-2-yl)-3-(2,2,2-trifluoroethyl)-3H-pyrrolo[2,3-d]pyrimidin-4(7H)-one (53.6 mg, 0.174 mmol) in anhydrous DMF (1.8 ml) at 0° C. was added bromine (9.85 μl, 0.191 mmol) and the mixture stirred for 5 min. Further bromine (9.85 μl, 0.191 mmol) was added and the mixture stirred for 5 min. The mixture was partitioned between ethyl acetate (5 ml) and an aqueous mixture (3:1:4, water, saturated sodium hydrogen carbonate (aq) solution and 20% w/w sodium thiosulfate (aq) solution, 20 ml). The aqueous phase was separated and extracted with ethyl acetate (3×5 ml). The combined ethyl acetate fractions were washed with brine/water (1:1, 4×5 ml), dried (anhydrous sodium sulfate), filtered and reduced in vacuo. The resulting residue was purified by silica gel chromatography (0-5% methanol in ethyl acetate) to afford the title compound (46.8 mg, 70%). LCMS RT=0.74 min, [M+H+(79Br)]=387.0, [M+H+(81Br)]=389.0.

Provenance & Evidence