Iodine → HCID 69431783, compound

Participants

Reaction Steps

To a solution of 7-[(4-methylphenyl)sulfonyl]4-pyridin-3-yl-7H-pyrrolo[2,3-d]pyrimidine [1 g, Reference Example 2] in tetrahydrofuran (20 mL) at −78° C. was added drop wise a solution of butyl lithium in hexane (2 mL, 1.6M) under inert atmosphere. The solution was stirred at that temperature for 1.5 hour and iodine (796 mg) was added. The reaction mixture was stirred at −78° C. for another 1 hour and allowed to reach room temperature. The reaction mixture was partitioned between ethyl acetate and aqueous sodium sulfite solution. The organic phase was separated, then dried over magnesium sulfate and then evaporated under reduced pressure. The residue was subjected to flash column chromatography on silica eluting with a gradient of ethyl acetate and cyclohexane (50:50, to 100, v/v) to give the title compound (260 mg) as an amorphous solid. MS: 477 [MH]+. LCMS (Method B) RT=3.26 minutes.

Provenance & Evidence