Bromocyclopentane → 4-Chloro-7-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidine

Participants

Reaction Conditions

Reaction Steps

NaH (3.8 g, 95.3 mmol) was added to a solution of 4-Chloro-7H-pyrrolo[2,3-d]pyrimidine (10 g, 63.5 mmol) in DMF (50 mL) at 0° C. The resulting mixture was stirred at 0° C. for 30 min, then warmed to room temperature. At this time Cyclopentylbromide (18.9 g, 127 mmol) was added and the reaction was heated to 60° C. After 4 h the reaction was cooled to 0° C. and quenched with water. The aqueous layer was extracted with EtOAc (3×), the combined organic layers were washed with water (1×), dried over Na2SO4, and concentrated. Purification by flash column chromatography (Hexanes/Ethyl acetate 9:1) afforded the title compound as a clear oil (10.6 g, 75%). MS: 222.1/224.1 (MH+); HPLC Rf: 5.77 min. (HPLC method 4).

Provenance & Evidence