Methanol → 2-Amino-5-chloro-3-methoxypyrazine

HRID 1378352Notes

Reaction equation

HRID 1378352 reaction equation
[Na].[NH2:2][C:3]1[C:8](Br)=[N:7][C:6]([Cl:10])=[CH:5][N:4]=1.[OH2:11].[CH3:12]O>>[NH2:2][C:3]1[C:8]([O:11][CH3:12])=[N:7][C:6]([Cl:10])=[CH:5][N:4]=1

Participants

5

Reactant 4

HCID 887MethanolHCID 962WaterHCID 5360545SodiumHCID 104886093-Bromo-5-chloropyrazin-2-amine

Product 1

HCID 107970362-Amino-5-chloro-3-methoxypyrazine

Procedure

Sodium (2.82 g) was dissolved in dry methanol (50 ml) under argon and 2-amino-3-bromo-5-chloropyrazine (1.68 g) was added in small portions at ambient temperature with stirring. The resulting stirred solution was heated under reflux and an argon atmosphere for 4 hours. Water (10 ml) was added at ambient temperature and the solvent removed by evaporation. A further volume of water (10 ml) was added and the aqeous phase was extracted with dichloromethane (3×50 ml). Combined organic extracts were dried (MgSO4) and evaporated to give 2-amino-5-chloro-3-methoxypyrazine (1.28 g), m.p. 102°-103° C.; 1H NMR (d6DMSO): 3.90 (s, 3H), 7.53 (s, 1H); mass spectrum (+ve CI): 160 (M+H)+.

Workup

  1. stirringThe resulting stirred solution
  2. temperaturewas heated
  3. temperatureunder reflux
  4. customthe solvent removed by evaporation
  5. additionA further volume of water (10 ml) was added
  6. extractionthe aqeous phase was extracted with dichloromethane (3×50 ml)
  7. dry with materialCombined organic extracts were dried (MgSO4)
  8. customevaporated

Sources & evidence

ORD record
ord-dfc8574311534c23b8d7a87c23113a0c
Source dataset
uspto-grants-1997_09
Patent number
US05668137

Reaction notes

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