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

HRID 547567Notes

Reaction equation

HRID 547567 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([NH:15][C:16]([C:18]3[CH:23]=[CH:22][C:21]([N+:24]([O-])=O)=[CH:20][N:19]=3)=[O:17])=[CH:11][CH:10]=2)[CH:5]=[C:4]([CH3:27])[N:3]=1>[Pd].CO.C1COCC1>[NH2:24][C:21]1[CH:22]=[CH:23][C:18]([C:16]([NH:15][C:12]2[CH:11]=[CH:10][C:9]([NH:8][C:6]3[CH:5]=[C:4]([CH3:27])[N:3]=[C:2]([NH2:1])[N:7]=3)=[CH:14][CH:13]=2)=[O:17])=[N:19][CH:20]=1

Participants

4

Reactant 1

HCID 59458006N-{4-[(2-amino-6-methyl-4-pyrimidinyl)amino]phenyl}-5-nitro-2-pyridinecarboxamide

Product 1

HCID 594580005-amino-N-{4-[(2-amino-6-methyl-4-pyrimidinyl)amino]phenyl}-2-pyridinecarboxamideYield 135.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

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%.

Workup

  1. filtrationThe reaction mixture was filtered
  2. customevaporated to dryness
  3. customrecrystallized from DCM/Pet

Sources & evidence

ORD record
ord-2f551363b75742faa7f705c7e045f822
Source dataset
uspto-grants-2011_05
Patent number
US07939546B2

Reaction notes

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