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

HRID 1510665

Reaktionsgleichung

Reaktionsgleichung von HRID 1510665
[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

Komponenten

4

Edukt 2

HCID 23694274Sodium methanolate methanolHCID 57815271HCID 57815271, Verbindung

Produkt 1

HCID 578153663-Methoxypyrido[2,3-b]pyrazin-6(5H)-oneAusbeute 94,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-a601dbe263bf4af288cf00bc76008191
Quelldatensatz
uspto-grants-2012_07
Patentnummer
US08211908B2

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