3-(4-Methylpiperazin-1-yl)-5-nitropyridin-4-amine → 5-(4-Methylpiperazin-1-yl)pyridine-3,4-diamine

HRID 1497843Notes

Reaction equation

HRID 1497843 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:9]=[N:10][CH:11]=[C:12]([N+:15]([O-])=O)[C:13]=2[NH2:14])[CH2:4][CH2:3]1>CO.[Pd]>[CH3:1][N:2]1[CH2:3][CH2:4][N:5]([C:8]2[C:13]([NH2:14])=[C:12]([NH2:15])[CH:11]=[N:10][CH:9]=2)[CH2:6][CH2:7]1

Participants

4

Reactant 1

HCID 866983293-(4-Methylpiperazin-1-yl)-5-nitropyridin-4-amine

Product 1

HCID 583776555-(4-Methylpiperazin-1-yl)pyridine-3,4-diamineYield 99%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 3-(4-methylpiperazin-1-yl)-5-nitropyridin-4-amine (LXX) (382 mg, 1.61 mmol) in MeOH (11 mL) was added 10% Pd/C. The solution was purged with hydrogen and stirred at room temperature under hydrogen for 4 h. The suspension was filtered through Celite® and the concentrated under vacuum to produce 5-(4-methylpiperazin-1-yl)pyridine-3,4-diamine (LXXI) as purple solid (330 mg, 1.59 mmol, 99% yield). 1H NMR (DMSO-d6, 500 MHz,): δ 2.18 (s, 3H), 2.34-2.36 (m, 4H), 3.13-3.16 (m, 4H), 3.89 (s, 2H), 5.20 (s, 2H), 5.94 (s, 1H), 7.31 (s, 1H); ESIMS found C10H17N5 m/z 208 (M+H).

Workup

  1. customThe solution was purged with hydrogen
  2. filtrationThe suspension was filtered through Celite®
  3. concentrationthe concentrated under vacuum

Sources & evidence

ORD record
ord-15f2400ced1042d8ab2b954049842b22
Source dataset
uspto-grants-2015_12
Patent number
US09199991B2

Reaction notes

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