3-[(2-Amino-6-methyl-4-pyrimidinyl)amino]-N-(4-nitrophenyl)benzamide hydrochloride → 3-[(2-Amino-6-methyl-4-pyrimidinyl)amino]-N-(4-aminophenyl)benzamide hydrochloride

Participants

Reaction Steps

To a suspension of compound B2 (1.41 g, 3.51 mmol) in (MeOH) 30 (mL) was added 10% Pd/C (20 mg) and hydrogenated under 45 Hg mm for 5 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 B3 (758 mg, 58%); m.p. (MeOH/EtOAc); 1H NMR [(CD3)2SO] δ12.70 (br, 1 H, NH), 10.83 (br s, 1 H, NH), 10.43 (s, 1 H, NH), 9.70 (v br, 2 H, NH2), 8.05-7.84 (br m, 2 H, ArH), 7.85-7.75 (m, 4 H, ArH & NH2), 7.55 (t, J=7.9 Hz, 1 H, ArH), 7.28 (d, J=8.7 Hz, 2 H, ArH), 6.24 (s, 1 H, ArH), 2.30 (s, 3 H, CH3); mass APCI+ 335.

Provenance & Evidence