Methanol → 3-Amino-1-methoxy-pyrazine-2-carboxylic acid methyl ester

HRID 81617Notes

Reaction equation

HRID 81617 reaction equation
[H-].[Na+].[CH3:3][O:4][C:5]([C:7]1[C:12]([NH2:13])=[N:11][C:10](Cl)=[CH:9][N:8]=1)=[O:6].[NH4+].[Cl-].[CH3:17][OH:18]>>[CH3:3][O:4][C:5]([CH:7]1[C:12]([NH2:13])=[N:11][CH:10]=[CH:9][N:8]1[O:18][CH3:17])=[O:6]

Participants

5

Reactant 4

HCID 887MethanolHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 53417426Methyl 3-amino-5-chloropyrazine-2-carboxylate

Product 1

HCID 867165353-Amino-1-methoxy-pyrazine-2-carboxylic acid methyl ester

Procedure

At 0° C. 75 mg (1.866 mmol) 60% sodium hydride in oil was added in portions to 5 ml MeOH and the mixture was stirred at room temperature for 30 min. After re-cooling to 0° C. 350 mg (1.866 mmol) 3-amino-5-chloro-pyrazine-2-carboxylic acid methyl ester (GB 1248146) was added and the mixture was allowed to warm to room temperature and stirred over night. Saturated aqueous NH4Cl was added and the mixture was extracted with DCM and EtOAc, the combined organic layers were washed with saturated aqueous sodium chloride, dried with Na2SO4 and evaporated. The residue was purified by chromatography on silica gel (cyclohexane to EtOAc) to provide the title compound as colorless solid.

Workup

  1. customAt 0° C
  2. temperatureAfter re-cooling to 0° C
  3. temperatureto warm to room temperature
  4. stirringstirred over night
  5. extractionthe mixture was extracted with DCM and EtOAc
  6. washthe combined organic layers were washed with saturated aqueous sodium chloride
  7. dry with materialdried with Na2SO4
  8. customevaporated
  9. customThe residue was purified by chromatography on silica gel (cyclohexane to EtOAc)

Sources & evidence

ORD record
ord-6d3d4828eded4a88a10af5f9ef078b90
Source dataset
uspto-grants-2014_09
Patent number
US08846658B2

Reaction notes

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