3-[(2,6-Diamino-4-pyrimidinyl)amino]-N-(4-nitrophenyl)benzamide hydrochloride → N-(4-Aminophenyl)-3-[(2,6-diamino-4-pyrimidinyl)amino]benzamide hydrochloride

Participants

Reaction Steps

To a suspension of compound B5 (567 mg, 1.41 mmol) in (MeOH) (30 mL) was added 10% Pd/C (20 mg) and hydrogenated under 40 Hg mm for 6 h. The reaction mixture was filtered through a pad of celite and the filtrate was evaporated to dryness. The residue was dissolved in a small volume of MeOH then 1 ml of 1.25M HCl in MeOH was added, stirred 10 min and evaporated to dryness. The residue was recrystallized from MeOH/EtOAc to give B6 (398 mg, 76%); mp (MeOH/EtOAc)>300° C., 1H NMR [(CD3)2SO] δ10.37 (s, 1 H, NH), 9.93 (s, 1 H, NH), 7.92-7.80 (m, 4 H, ArH & NH2), 7.68 (d, J=7.7 Hz, 1 H, ArH), 7.61 (br s, 2 H, NH2), 7.49-7.45 (m, 3 H, ArH), 7.24 (br d, J=8.7 Hz, 2 H, ArH), 5.45 (s, 1 H, ArH), mass APCI+ 336.

Provenance & Evidence