Dimethylamine → 5-Bromo-N~3~,N~3~-dimethylpyrazine-2,3-diamine

HRID 343371Notes

Reaction equation

HRID 343371 reaction equation
[NH2:1][C:2]1[C:7](Br)=[N:6][C:5]([Br:9])=[CH:4][N:3]=1.[CH3:10][NH:11][CH3:12]>C(O)C>[NH2:1][C:2]1[C:7]([N:11]([CH3:12])[CH3:10])=[N:6][C:5]([Br:9])=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 674DimethylamineHCID 6200042-Amino-3,5-dibromopyrazine

Product 1

HCID 142076275-Bromo-N~3~,N~3~-dimethylpyrazine-2,3-diamine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-Amino-3,5-dibromopyrazine (1.0 g) was dissolved in a solution of dimethylamine in ethanol (33% w/v; 20 ml) and the solution was heated under reflux for 18 hours. Volatile material was removed by evaporation and the residue was purified by elution with dichloromethane through a silica gel Mega Bond Elut column to give 2-amino-5-bromo-3-dimethylaminopyrazine (0.67 g); 1H NMR (d6 -DMSO): 2.75 (s, 6H), 6.1-6.2 (br s, 2H), 7.6 (s, 1H); mass spectrum (+ve CI): 217 (M+H)+.

Workup

  1. temperaturethe solution was heated
  2. temperatureunder reflux for 18 hours
  3. customVolatile material was removed by evaporation
  4. customthe residue was purified by elution with dichloromethane through a silica gel Mega Bond Elut column

Sources & evidence

ORD record
ord-f24838784ab54c62a27f41a81e8cf8dd
Source dataset
uspto-grants-1999_01
Patent number
US05861401

Reaction notes

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