Ethanol → HCID 86719385, compound

Participants

Reaction Conditions

Reaction Steps

A suspension of 6-chloro-5-(4-chlorophenyl)-7-(3-nitrophenyl)-7H-pyrrolo[2,3-d]pyrimidin-4-ylcarbamate (20) (1.3 g, 2.6 mmol), iron powder (2.9 g, 52.1 mmol) and NH4Cl (1.4 g, 26.0 mmol) in a mixture of THF (30 mL), H2O (15 mL) and EtOH (3 mL) was purged with N2 before heated to 50° C. for 8 hrs. The reaction was then cooled down to r.t. and was filtered through Celite pad. The filter cake was thoroughly washed with DCM. The filtrate was washed with H2O, brine, dried over Na2SO4 and concentrated. The crude product was purified by column chromatographic (silica gel, with 0 to 50% EA in a mixture of PE & DCM (1:1) and then 0 to 10% MeOH in DCM) to afford tert-butyl 7-(3-aminophenyl)-6-chloro-5-(4-chlorophenyl)-7H-pyrrolo[2,3-d]pyrimidin-4-ylcarbamate (21) (421 mg, 35% yield) as a yellow solid. LC-MS (ESI): m/z (M/M+2) 468.6/470.6.

Provenance & Evidence