Methanol → 6-(Morpholin-4-yl)pyridine-3,4-diamine

HRID 1487999Notes

Reaction equation

HRID 1487999 reaction equation
[N:1]1([C:7]2[CH:12]=[C:11]([NH2:13])[C:10]([N+:14]([O-])=O)=[CH:9][N:8]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.CO>[Pd].C1COCC1>[O:4]1[CH2:5][CH2:6][N:1]([C:7]2[N:8]=[CH:9][C:10]([NH2:14])=[C:11]([NH2:13])[CH:12]=2)[CH2:2][CH2:3]1

Participants

5

Reactant 2

HCID 887MethanolHCID 900216182-(Morpholin-4-yl)-5-nitropyridin-4-amine2×

Product 1

HCID 900211616-(Morpholin-4-yl)pyridine-3,4-diamineYield 92.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Into a 50-mL round-bottom flask were placed 2-(morpholin-4-yl)-5-nitropyridin-4-amine (compound 151.1, 350 mg, 1.56 mmol), methanol (20 mL), THF (10 mL), and Pd/C (35 mg). The above solution was purged with N2 and then H2. The reaction mixture was stirred for 4 h at room temperature. The solids were filtered out. The resulting mixture was concentrated under reduced pressure. This resulted in 280 mg (92%) of the title compound as a pink solid.

Workup

  1. customInto a 50-mL round-bottom flask were placed
  2. customThe above solution was purged with N2
  3. filtrationThe solids were filtered out
  4. concentrationThe resulting mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-7e1d9f9f72884670bf1f31413599f3a7
Source dataset
uspto-grants-2016_08
Patent number
US09428502B2

Reaction notes

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