5-Iodo-7-isopropyl-7H-pyrrolo[2,3-d]pyrimidine → (5-Bromo-6-ethoxy-pyridin-3-yl)-(7-isopropyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-methanone

Participants

Reaction Steps

A solution of 5-Iodo-7-isopropyl-7H-pyrrolo[2,3-d]pyrimidine (Preparation 93, 530 mg, 1.85 mmol) in anhydrous diethyl ether (8 mL) was cooled to −78° C. under nitrogen and n-BuLi (1 mL of a 2.03M solution in Hexane, 2.03 mmol) was added drop wise over a period of 10 min. Just after the completion of addition of n-BuLi, a solution of 5-Bromo-6-ethoxy-N-methoxy-N-methyl-nicotinamide (Preparation 240) in anhydrous diethyl ether (7 mL) was added slowly to the mixture and it was stirred at the same temperature for another 1 hour. The reaction mixture was warmed to room temperature and allowed to stir for another hour before being quenched with sat. aq. NH4Cl (15 mL). The mixture was extracted with EtOAc (3×15 mL), washed with water (20 mL), brine (15 mL), dried (Na2SO4) and evaporated in vacuo. The crude material was purified by column chromatography on silica gel (EtOAc:petroleum ether 2:10) to afford the title compound as a yellow gum in 49% yield, 350 mg.

Provenance & Evidence