Ammonium Chloride → HCID 86689035, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of tert-butyl 3-iodo-1-(4-nitrophenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-ylcarbamate (28) (4.29 g, 8.7 mmol) in THF/EtOH/H2O (40 mL/20 mL/10 mL) was added Fe powder (2.43 g, 43.45 mmol) and NH4Cl (4.65 g, 86.9 mmol). The resulting mixture was purged with N2 before heated to 50° C. for 2 h. The mixture was cooled and filtered through a Celite pad. The solvents were evaporated and the residue was separated in DCM and water. The aqueous layer was extracted with DCM (×4). The combined organic layers were dried over Na2SO4. Solvent was removed under vacuum and purified by flash chromatography (0-60% EA in PE with 0.5% TEA) to provide tert-butyl 1-(4-aminophenyl)-3-iodo-1H-pyrazolo[3,4-d]pyrimidin-4-ylcarbamate (29) (3.4 g, 86%) as a yellow solid. LC-MS (ESI): m/z (M+1) 453.0.

Provenance & Evidence