N-{3-[(2,5-dichloropyrimidin-4-yl)amino]benzyl}-3-nitrobenzamide → 3-Amino-N-{3-[(2,5-dichloropyrimidin-4-yl)amino]benzyl}benzamide

Participants

Reaction Conditions

Reaction Steps

To a solution N-{3-[(2,5-dichloropyrimidin-4-yl)amino]benzyl}-3-nitrobenzamide (400.0 mg, 0.956 mmol) in water (0.7 mL), methanol (3.7 mL) and acetic acid (1.5 mL) was added iron (130 mg, 2.4 mmol) powder in small quantities. When the addition was completed, the very cloudy mixture was stirred at 0° C. for 1 h and then heat at 40° C. for 3 h. The mixture was filtered, and the cake was washed with MeOH/EtOAc. The filtrate was concentrated and the residue was diluted with H2O, then the aqueous layer was extracted with EtOAc three times. The combined organic layers were dried, filtered and concentrated to give the desired product as an off-white powder (435 mg). LCMS for C18H15Cl2N5O (M+H)+: m/z=388.0, 390.0, 392.0. 1H NMR (400 MHz, CD3OD): δ 8.20 (s, 1H), 7.59 (t, J=2.0 Hz, 1H), 7.52 (d, J=8.0 Hz, 1H), 7.36 (t, J=8.0 Hz, 1H), 7.24 (m, 2H), 7.20 (m, 2H), 6.93 (m, 1H), 4.60 (s, 2H).

Provenance & Evidence