Sodium methanolate methanol → 3-Methoxypyrido[2,3-b]pyrazin-6(5H)-one

HRID 385545

Reaction equation

HRID 385545 reaction equation
[NH2:1][C:2]1[C:3](/[CH:10]=[CH:11]/[C:12]([O:14]CC)=O)=[N:4][CH:5]=[C:6]([O:8][CH3:9])[N:7]=1.C[O-].[Na+].CO>C(O)C>[CH3:9][O:8][C:6]1[N:7]=[C:2]2[NH:1][C:12](=[O:14])[CH:11]=[CH:10][C:3]2=[N:4][CH:5]=1

Participants

4

Reactant 2

HCID 23694274Sodium methanolate methanolHCID 57815271HCID 57815271, compound

Product 1

HCID 578153663-Methoxypyrido[2,3-b]pyrazin-6(5H)-oneYield 94.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 0.85 g of ethyl (2E)-3-(3-amino-5-methoxypyrazin-2-yl)acrylate in 40 mL of ethanol, 2.20 g of a 28% sodium methoxide/methanol solution was added, and the mixture was heated under reflux while stirring for 7 hours 30 minutes. The reaction mixture was cooled to room temperature, the solvent was then distilled off under reduced pressure, and to the resultant residue, water, a saturated aqueous ammonium chloride solution and chloroform were added, the organic layer was separated, and the aqueous layer was added with sodium chloride and extracted with chloroform. The organic layer and the extract were combined, the resultant solution was washed with a saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. Diethyl ether was added to the resultant residue, and the solid was filtered off and washed with diethyl ether to obtain 0.64 g of 3-methoxypyrido(2,3-b)pyrazin-6(5H)-one as a light yellow solid.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux
  3. distillationthe solvent was then distilled off under reduced pressure
  4. additionto the resultant residue, water, a saturated aqueous ammonium chloride solution and chloroform were added
  5. customthe organic layer was separated
  6. additionthe aqueous layer was added with sodium chloride
  7. extractionextracted with chloroform
  8. washthe resultant solution was washed with a saturated aqueous sodium chloride solution
  9. dry with materialdried over anhydrous magnesium sulfate
  10. distillationthe solvent was distilled off under reduced pressure
  11. additionDiethyl ether was added to the resultant residue
  12. filtrationthe solid was filtered off
  13. washwashed with diethyl ether

Sources & evidence

ORD record
ord-9e6f05dc08e2404e8be9d6a8c9213700
Source dataset
uspto-grants-2013_02
Patent number
US08367831B2

Linked notes

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