2-Amino-3-bromo-5-methylpyrazine → 3-Methoxy-5-methyl-2-pyrazinamine

HRID 2287380Notes

Reaction equation

HRID 2287380 reaction equation
[NH2:1][C:2]1[C:7](Br)=[N:6][C:5]([CH3:9])=[CH:4][N:3]=1.[CH3:10][O-:11].[Na+]>CO>[NH2:1][C:2]1[C:7]([O:11][CH3:10])=[N:6][C:5]([CH3:9])=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 98990432-Amino-3-bromo-5-methylpyrazineHCID 10942334Sodium Methoxide

Product 1

HCID 107018943-Methoxy-5-methyl-2-pyrazinamineYield 75%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2-Amino-3-bromo-5-methylpyrazine (0.374 g) was added to a freshly prepared solution of sodium methoxide in methanol (made by addition of sodium (0.115 g) to methanol (6 ml)). The reaction was heated under reflux for 18 hours, cooled to ambient temperature and the solvent removed by evaporation. Water (5 ml) was added to the residue and extracted with dichloromethane (3×20 ml). The combined organic extracts were dried (MgSO4) and the solvent removed by evaporation. The residue was purified by chromatography on silica gel, eluting with dichloromethane to give 2-amino-3-methoxy-5-methylpyrazine as a white crystalline solid (0.208 g, 75%), m.p. 67-69° C.; mass spectrum (+ve CI): 140 (M+H)+.

Workup

  1. temperatureThe reaction was heated
  2. temperatureunder reflux for 18 hours
  3. customthe solvent removed by evaporation
  4. additionWater (5 ml) was added to the residue
  5. extractionextracted with dichloromethane (3×20 ml)
  6. dry with materialThe combined organic extracts were dried (MgSO4)
  7. customthe solvent removed by evaporation
  8. customThe residue was purified by chromatography on silica gel
  9. washeluting with dichloromethane

Sources & evidence

ORD record
ord-8ca4cddcc6234b7987da8d3759fe00db
Source dataset
uspto-grants-2000_07
Patent number
US06083951

Reaction notes

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