Methylamine → 5-Bromo-N~3~-methylpyrazine-2,3-diamine

HRID 1086171Notes

Reaction equation

HRID 1086171 reaction equation
[CH3:1][NH2:2].Br[C:4]1[C:5]([NH2:11])=[N:6][CH:7]=[C:8]([Br:10])[N:9]=1>C(O)C>[NH2:11][C:5]1[C:4]([NH:2][CH3:1])=[N:9][C:8]([Br:10])=[CH:7][N:6]=1

Participants

4

Reactant 2

HCID 6329MethylamineHCID 6200042-Amino-3,5-dibromopyrazine

Product 1

HCID 121985205-Bromo-N~3~-methylpyrazine-2,3-diamineYield 40%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
130 °C

Procedure

1.55 g (50 mmol) of 40% strength aqueous methylamine solution is added to a solution of 2.53 g (10 mmol) of 3,5-dibromo-2-aminopyrazine in ethanol. The mixture is stirred in an autoclave at 130° C. for 17 hours. After evaporation of the solvent under reduced pressure, the product is purified by chromatography on a silica column (eluant=CH2Cl2, to which 3% of CH3OH has been added). 0.8 g (Yld=40%) of 2-amino-5-bromo-3-methylaminopyrazine (m.p. 121° C.) is obtained.

Workup

  1. customAfter evaporation of the solvent under reduced pressure
  2. customthe product is purified by chromatography on a silica column (eluant=CH2Cl2, to which 3% of CH3OH has been added)

Sources & evidence

ORD record
ord-5b64c1009c9b4dc2b6f3c8e85a128999
Source dataset
uspto-grants-1991_07
Patent number
US05028605

Reaction notes

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