N,N-Dimethylaniline → 3,6-Dimethylpyrazin-2-amine

HRID 1615629

Reaction equation

HRID 1615629 reaction equation
[CH3:1][C:2]1[CH:7]=[N:6][C:5]([CH3:8])=[CH:4][N:3]=1.C[N:10](C)C1C=CC=CC=1>>[CH3:8][C:5]1[C:4]([NH2:10])=[N:3][C:2]([CH3:1])=[CH:7][N:6]=1

Participants

3

Reactant 2

HCID 949N,N-DimethylanilineHCID 312522,5-Dimethylpyrazine

Product 1

HCID 132615003,6-Dimethylpyrazin-2-amineYield 10%

Conditions

Temperature
170 °C

Procedure

A mixture of 2,5-dimethylpyrazine (14 g, 0.13 mol) in N,N-dimethylaniline (50 mL) was heated to 170° C. and NaNH2 (22 g, 0.56 mol) was added in portions. The reaction mixture was stirred at 170° C. for 1 h, and the solvent was removed. The product was purified by silica gel column chromatography to give 3,6-dimethylpyrazin-2-amine as a brown solid (1.6 g, yield 10%). ESI MS: m/z 124 [M+1]+.

Workup

  1. customthe solvent was removed
  2. customThe product was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-b9faeb1e32b6465cad7c93bc6c5a4074
Source dataset
uspto-grants-2014_07
Patent number
US08765760B2

Linked notes

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