N-Iodosuccinimide → 6-Chloro-7-iodo-7-deazapurine

Participants

Reaction Steps

To 4-chloro-7H-pyrrolo[2,3-d]pyrimidine (1, 1.21 g, 7.88 mmol) dissolved in 50 mL of dichloromethane, N-iodosuccinimide (1.95 g, 8.67 mmol) is added and the reaction is stirred at room temperature overnight. The reaction is quenched with 50% aqueous sodium thiosulfate and the mixture is filtered through celite. The aqueous layer is extracted with ethyl acetate. The organic layers are combined and washed with water, then brine, and dried with sodium sulfate, filtered and the filtrate concentrated under vacuum. The resulting material is purified by silica gel column chromatography, eluting with ethyl acetate and dichloromethane. Appropriate fractions are combined and concentrated under vacuum to provide the desired compound (27, 1.383 g). MS (ESI) [M+H+]+=279.8, 281.8.

Provenance & Evidence