(2-Methoxy-ethyl)-(5-nitro-pyrazin-2-yl)-amine → N-(2-methoxy-ethyl)-pyrazine-2,5-diamine

HRID 719989Notes

Reaction equation

HRID 719989 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][NH:5][C:6]1[CH:11]=[N:10][C:9]([N+:12]([O-])=O)=[CH:8][N:7]=1>C(OCC)(=O)C.[Pd]>[CH3:1][O:2][CH2:3][CH2:4][NH:5][C:6]1[CH:11]=[N:10][C:9]([NH2:12])=[CH:8][N:7]=1

Participants

4

Reactant 1

HCID 21897383(2-Methoxy-ethyl)-(5-nitro-pyrazin-2-yl)-amine

Product 1

HCID 21897315N-(2-methoxy-ethyl)-pyrazine-2,5-diamineYield 80.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of (2-methoxy-ethyl)-(5-nitro-pyrazin-2-yl)-amine (290 mg, 1.46 mmol) in ethyl acetate (25 mL) was treated with 10% palladium on activated carbon (40 mg). The reaction mixture was then placed on a Parr shaker under a hydrogen atomsphere of 50 psi for 4 h. The catalyst was then filtered off through a pad of celite, and the celite pad was then washed well with ethyl acetate. The filtrate was then concentrated in vacuo. Biotage chromatography (FLASH 12M, Silica, 98/2 to 95/5 methylene chloride/methanol) afforded N-(2-methoxy-ethyl)-pyrazine-2,5-diamine (198 mg, 80%) as an orange solid: EI-HRMS m/e calcd for C7H12N4O (M+) 168.1011, found 168.1018.

Workup

  1. filtrationThe catalyst was then filtered off through a pad of celite
  2. washthe celite pad was then washed well with ethyl acetate
  3. concentrationThe filtrate was then concentrated in vacuo

Sources & evidence

ORD record
ord-2dd21bcbd7214dbe9f9889be1885bff9
Source dataset
uspto-grants-2006_11
Patent number
US07132425B2

Reaction notes

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