N-bromobutanimide → 5-Bromo-4-chloro-7-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidine

Participants

Reaction Steps

N-Bromosuccinimide (15.4 g, 86.8 mmol) was added to a solution of 4-Chloro-7-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidine (15.4 g, 69.5 mmol) in CH2Cl2 (100 mL). After 12 h the reaction was quenched with saturated aqueous NaHCO3 (100 mL). The layers were separated and the aqueous layer was extracted with CH2Cl2 (2×100 mL). The combined organic layers were dried over Na2SO4 and concentrated. Purification by flash column chromatography (hexanes/ethyl acetate 9:1) afforded the title compound as a white solid (12.8 g, 61%). MS: 300.1/302.0/304.1 (MH+); HPLC Rf: 6.68 min. (HPLC method 4).

Provenance & Evidence