Ethanol → N-(5-cyclopropyl-1H-pyrazol-3-yl)-2-phenyl-pyrimidine-4,5-diamine

Participants

Reaction Conditions

Reaction Steps

A mixture of N-(5-cyclopropyl-1H-pyrazol-3-yl)-5-nitro-2-phenylpyrimidin-4-amine (500 mg, 1.55 mmol, 1.0 eq), NH4Cl (1.0 g, 19.39 mmol, 12.5 eq), EtOH (12 mL), THF (12 mL) and H2O (5 mL) was heated to reflux. Iron powder (0.59 g, 10.54 mmol, 6.8 eq) was added in three portions over 15 minutes under N2 atmosphere. The resulting mixture was continued to reflux for 1 hour, cooled down to 23° C., diluted with CH2Cl2 and filtered through celite. The organic phase was washed (brine), dried (Na2SO4), filtered and concentrated to give target product N-(5-cyclopropyl-1H-pyrazol-3-yl)-2-phenylpyrimidine-4,5-diamine (Compound 5) (350 mg, 38.6%). LC-MS (m/z)=293.1 [M+H]+. 1H-NMR (300 MHz, DMSO-d6): δ 0.71-0.72 (m, 2H), 0.95-1.00 (m, 2H), 1.92-1.95 (m, 1H), 5.29 (s, 2H), 6.59 (s, 1H), 7.31-7.43 (m, 3H), 7.81 (s, 1H), 8.18 (d, J=6.9 Hz, 2H), 8.81 (s, 1H), 12.02 (s, 1H).

Provenance & Evidence