2-Methoxy-4,6-dimethyl-5-nitropyrimidine → 2-Methoxy-4,6-dimethylpyrimidin-5-amine

HRID 1628512Notes

Reaction equation

HRID 1628512 reaction equation
[CH3:1][O:2][C:3]1[N:8]=[C:7]([CH3:9])[C:6]([N+:10]([O-])=O)=[C:5]([CH3:13])[N:4]=1>O1CCCC1.[Pd]>[CH3:1][O:2][C:3]1[N:4]=[C:5]([CH3:13])[C:6]([NH2:10])=[C:7]([CH3:9])[N:8]=1

Participants

4

Reactant 1

HCID 687373032-Methoxy-4,6-dimethyl-5-nitropyrimidine

Product 1

HCID 687393852-Methoxy-4,6-dimethylpyrimidin-5-amineYield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-methoxy-4,6-dimethyl-5-nitropyrimidine (3.37 g, 18.4 mmol) in tetrahydrofuran (80 mL) was added 10% palladium on carbon (50% wet, 330 mg), and the mixture was purged with hydrogen and stirred under balloon pressure hydrogen at room temperature for 4 hours. The catalyst was removed by filtration, and the filtrate was concentrated in vacuo to give the title compound as a pale yellow solid (2.82 g, 18.4 mmol, 100%).

Workup

  1. customthe mixture was purged with hydrogen
  2. customThe catalyst was removed by filtration
  3. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-cd5fa3570f0f4d53a4c847201290f489
Source dataset
uspto-grants-2014_07
Patent number
US08785460B2

Reaction notes

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