HCID 21897385, compound → HCID 20310356, compound

HRID 719875Notes

Reaction equation

HRID 719875 reaction equation
[CH3:1][N:2]([CH3:12])[C:3]1[CH:4]=[N:5][C:6]([N+:9]([O-])=O)=[CH:7][N:8]=1.[H][H]>C(O)C.[Pd]>[CH3:1][N:2]([CH3:12])[C:3]1[N:8]=[CH:7][C:6]([NH2:9])=[N:5][CH:4]=1

Participants

5

Reactant 2

HCID 21897385HCID 21897385, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 20310356HCID 20310356, compoundYield 75%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of dimethyl-(6-nitro-pyrazin-3-yl)-amine (1.27 g, 7.55 mmol) in ethanol (90 mL) was treated with 10% palladium on activated carbon (0.40 g). The reaction mixture was stirred under a positive pressure of hydrogen gas (balloon) at 25° C. and atmospheric pressure overnight. The catalyst was then filtered off through a pad of celite, and the celite pad was washed well with ethanol. The filtrate was concentrated in vacuo, and the resulting black-orange solid was triturated with petroleum ether to afford N5,N5-dimethyl-pyrazine-2,5-diamine (0.78 g, 75%) as a black solid: mp 71.5–74.2° C.; EI-HRMS m/e calcd for C6H10N4 (M+) 138.0905, found 138.0903.

Workup

  1. customatmospheric pressure overnight
  2. filtrationThe catalyst was then filtered off through a pad of celite
  3. washthe celite pad was washed well with ethanol
  4. concentrationThe filtrate was concentrated in vacuo
  5. customthe resulting black-orange solid was triturated with petroleum ether

Sources & evidence

ORD record
ord-e680a32f3dbe4cd18c42689a6d8d3c97
Source dataset
uspto-grants-2006_11
Patent number
US07132425B2

Reaction notes

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