N-{4-[(2-amino-6-methyl-4-pyrimidinyl)amino]phenyl}-5-nitro-2-pyridinecarboxamide → 5-amino-N-{4-[(2-amino-6-methyl-4-pyrimidinyl)amino]phenyl}-2-pyridinecarboxamide

Participants

Reaction Steps

To a suspension of 20 (523 mg, 1.43 mmol) was suspended in 1:1 MeOH/THF (100 ml) was added 10% Pd/C (100 mg) and hydrogenated at 55 Hg mm. for 5 h. The reaction mixture was filtered and evaporated to dryness and recrystallized from DCM/Pet.ether to give 21 (649 mg, 96%); mp (DCM/Pet.ether)>290° C.; 1H NMR [(CD3)2SO] δ 10.05 (s, 1 H, NH), 8.85 (s, 1 H, NH), 8.25 (d, J=2.5 Hz, 1 H, H-6), 7.82 (d, J=8.6 Hz, 1 H, H-3), 7.73 (d, J=9.0 Hz, 2 H, H-2′,6′), 7.60 (d, J=9.0 Hz, 2 H, H-3′,5′), 7.03 (dd, J=8.5, 2.7 Hz, 1 H, H-4), 6.04 (brs, 2 H, NH2), 6.03 (brs, 2 H, NH2), 5.85 (s, 1 H, H-5″), 2.08 (s, 3 H, CH3); Anal. calc. for C17H17N7).0.25H2O C, 60.1; H, 5.2; N, 28.9; found, C, 60.0; H, 5.2; N, 28.7%.

Provenance & Evidence