3-Morpholino-5-nitropyridin-4-amine → 5-Morpholinopyridine-3,4-diamine

HRID 82075Notes

Reaction equation

HRID 82075 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[CH:8]=[N:9][CH:10]=[C:11]([N+:14]([O-])=O)[C:12]=2[NH2:13])[CH2:3][CH2:2]1>CO.[Pd]>[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[C:12]([NH2:13])=[C:11]([NH2:14])[CH:10]=[N:9][CH:8]=2)[CH2:3][CH2:2]1

Participants

4

Reactant 1

HCID 583779133-Morpholino-5-nitropyridin-4-amine

Product 1

HCID 583779865-Morpholinopyridine-3,4-diamineYield 37%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 3-morpholino-5-nitropyridin-4-amine (LIII) (1 eq) in MeOH was added 10% Pd/C. The solution was purged with hydrogen and stirred overnight at r.t. under hydrogen. The suspension was filtered through Celite and concentrated under vacuum to produce 5-morpholinopyridine-3,4-diamine (LIV) as a purple solid (37% yield). 1H NMR (DMSO-d6, 400 MHz,): δ 3.09-3.11 (m, 4H), 3.64-3.66 (m, 4H), 3.92 (s, 2H), 5.23 (s, 2H), 6.94 (s, 1H), 7.33 (s, 1H). ESIMS Found C9H14N4O m/z 195 (M+H).

Workup

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

Sources & evidence

ORD record
ord-f7a233cf39a1416795afaa5f8e21dae1
Source dataset
uspto-grants-2014_09
Patent number
US08846714B2

Reaction notes

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