n2-Methyl-5-nitropyrimidine-2,4-diamine → 2-N-methylpyrimidine-2,4,5-triamine

HRID 453381Notes

Reaction equation

HRID 453381 reaction equation
[CH3:1][NH:2][C:3]1[N:8]=[C:7]([NH2:9])[C:6]([N+:10]([O-])=O)=[CH:5][N:4]=1.[H][H]>[Pd].CO>[CH3:1][NH:2][C:3]1[N:8]=[C:7]([NH2:9])[C:6]([NH2:10])=[CH:5][N:4]=1

Participants

5

Reactant 2

HCID 255555n2-Methyl-5-nitropyrimidine-2,4-diamineHCID 178418361HCID 178418361, compound

Product 1

HCID 2553752-N-methylpyrimidine-2,4,5-triamine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

N2-methyl-5-nitropyrimidine-2,4-diamine 48 (0.83 g, 4.9 mmol) and 10% palladium on carbon (0.52 g, 0.49 mmol) were combined under nitrogen. Methanol (16 mL) was added, and the atmosphere replaced with hydrogen from a balloon. The reaction was stirred rapidly for 6 h, at which point the atmosphere was replaced with nitrogen and the reaction mixture was filtered through celite, rinsing with methanol. The filtrate was concentrated in vacuo to give N2-methylpyrimidine-2,4,5-triamine 49 as a light pink solid. MS (ES+): 140 (M+H)+; Calc. for C5H9N5=139.16.

Workup

  1. filtrationthe reaction mixture was filtered through celite
  2. washrinsing with methanol
  3. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-17ac83a2e780465282873696d3f87a85
Source dataset
uspto-grants-2013_07
Patent number
US08492404B2

Reaction notes

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