Ammonium Chloride → Tert-butyl 3-(5-amino-6-(dibenzylamino)pyrimidin-4-ylamino)phenyl(methyl)carbamate

Participants

Reaction Conditions

Reaction Steps

To a solution of tert-butyl 3-(6-(dibenzylamino)-5-nitropyrimidin-4-ylamino)phenyl(methyl)carbamate (21) (6.7 g, 12.4 mmol) in THF/MeOH/H2O (100 mL/50 mL/30 mL) was added Fe powder (3.47 g, 62 mmol) and NH4Cl (6.63 g, 124 mmol). The reaction mixture was heated at 50° C. for 5 h under N2. After cooling to rt, the reaction mixture was filtered through a pad of Celite. The filtrate was extracted with EtOAc (30 mL×3), washed with water and brine, dried over Na2SO4, and concentrated in vacuo to afford tert-butyl 3-(5-amino-6-(dibenzylamino)pyrimidin-4-ylamino)phenyl(methyl)carbamate (22) (6 g, yield 95%) as a yellow solid. LC-MS (ESI): m/z (M+1) 511.

Provenance & Evidence