4-[4-(Benzyloxy)butyl]-6-methoxypyrido[2,3-b]pyrazin-3(4H)-one → 4-(4-Hydroxybutyl)-6-methoxypyrido[2,3-b]pyrazin-3(4H)-one

HRID 1847038Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1847038
C([O:8][CH2:9][CH2:10][CH2:11][CH2:12][N:13]1[C:18](=[O:19])[CH:17]=[N:16][C:15]2[CH:20]=[CH:21][C:22]([O:24][CH3:25])=[N:23][C:14]1=2)C1C=CC=CC=1>C(OCC)(=O)C.ClCCl.[O-2].[O-2].[Mn+4]>[OH:8][CH2:9][CH2:10][CH2:11][CH2:12][N:13]1[C:18](=[O:19])[CH:17]=[N:16][C:15]2[CH:20]=[CH:21][C:22]([O:24][CH3:25])=[N:23][C:14]1=2

Komponenten

5

Edukt 1

HCID 867249624-[4-(Benzyloxy)butyl]-6-methoxypyrido[2,3-b]pyrazin-3(4H)-one

Produkt 1

HCID 867249634-(4-Hydroxybutyl)-6-methoxypyrido[2,3-b]pyrazin-3(4H)-oneAusbeute 88 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418406HCID 178418406, VerbindungKatalysatorHCID 6344DichloromethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of 4-[4-(benzyloxy)butyl]-6-methoxypyrido[2,3-b]pyrazin-3(4H)-one (847 mg, 2.5 mmol) in ethyl acetate (20 ml) 20% palladium hydroxide (400 mg) was added and the catalytic hydrogenation was carried out at room temperature for 90 minutes. After removing the catalyst by filtration, the solvent was removed under reduced pressure, the obtained residue was dissolved in dichloromethane (20 ml) to which manganese dioxide (1.09 g, 12.5 mmol) was then added, and the mixture was stirred overnight at room temperature. After removing manganese dioxide by filtration, the solvent of the filtrate was removed under reduced pressure and the obtained residue was purified by silica gel column chromatography (n-hexane/ethyl acetate) to yield 548 mg (88%) of the title compound in the form of a light brown solid.

Aufarbeitung

  1. customAfter removing the catalyst
  2. filtrationby filtration
  3. customthe solvent was removed under reduced pressure
  4. additionwas then added
  5. customAfter removing manganese dioxide
  6. filtrationby filtration
  7. customthe solvent of the filtrate was removed under reduced pressure
  8. customthe obtained residue was purified by silica gel column chromatography (n-hexane/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-12c944561158410e850bbc7500abe1e4
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08952010B2

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