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

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Reaction Steps

N-Bromosuccinimide (165 g, 926 mmol) was added to a solution of 4-Chloro-7-isopropyl-7H-pyrrolo[2,3-d]pyrimidine (151 g, 772 mmol) in CH2Cl2 (1 L). After 12 h the reaction was quenched with saturated aqueous NaHCO3 (500 mL). The layers were separated and the aqueous layer was extracted with CH2Cl2 (2×500 mL). The combined organic layers were washed with water (3×500 mL) and brine (1×500 mL), dried (Na2SO4), filtered, and concentrated in vacuo to afford the title compound as a white solid (198 g, 94%). MS: 275.5 (MH+); HPLC Rf: 5.99 min. (HPLC method 4).

Provenance & Evidence