Ammonium cerium (IV) nitrate → 3-Methoxypyrido[2,3-b]pyrazin-6(5H)-one

HRID 657076

Reaktionsgleichung

Reaktionsgleichung von HRID 657076
[CH3:1][O:2][C:3]1[N:8]=[C:7]2[N:9]=[C:10]([O:13]CC3C=CC(OC)=CC=3)[CH:11]=[CH:12][C:6]2=[N:5][CH:4]=1.[N+]([O-])([O-])=O.[Ce+4].[NH4+].[N+]([O-])([O-])=O.[N+]([O-])([O-])=O.[N+]([O-])([O-])=O.[N+]([O-])([O-])=O.CO.C(Cl)Cl>C(#N)C.O>[CH3:1][O:2][C:3]1[N:8]=[C:7]2[NH:9][C:10](=[O:13])[CH:11]=[CH:12][C:6]2=[N:5][CH:4]=1

Komponenten

6

Edukt 3

HCID 9869224Ammonium cerium (IV) nitrateHCID 21226129Dichloromethane methanolHCID 594373643-(Methyloxy)-6-({[4-(methyloxy)phenyl]methyl}oxy)pyrido[2,3-b]pyrazine

Produkt 1

HCID 578153663-Methoxypyrido[2,3-b]pyrazin-6(5H)-oneAusbeute 85 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittel2×HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

3-(Methyloxy)-6-({[4-(methyloxy)phenyl]methyl}oxy)pyrido[2,3-b]pyrazine (0.6 g, 2 mmol) was dissolved in acetonitrile (100 mL) and then ammonium cerium (IV) nitrate (1.09 g, 2 mmol) dissolved in water (50 mL) was added. The reaction was stirred at rt for 0.5 h and then 20% MeOH/DCM and water were added. The layers were separated and the aqueous was extracted with 20% MeOH/DCM twice more. The combined organic phases were dried, filtered and evaporated and the crude was purified by trituration with diethyl ether to afford the title compound (0.3 g, 85%).

Aufarbeitung

  1. additionwas added
  2. customThe layers were separated
  3. extractionthe aqueous was extracted with 20% MeOH/DCM twice more
  4. customThe combined organic phases were dried
  5. filtrationfiltered
  6. customevaporated
  7. customthe crude was purified by trituration with diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-ff176b7ae83c414aaf071d0f7341f5eb
Quelldatensatz
uspto-grants-2011_12
Patentnummer
US08071592B2

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