Water → 4-(3-{[tert-Butyl(diphenyl)silyl]oxy}-2-fluoropropyl)-6-methoxypyrido[2,3-b]pyrazin-3(4H)-one

HRID 1847022Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1847022
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[N:11]=[CH:10][C:9](=[O:12])[NH:8][C:7]=2[N:13]=1.[C:14]([Si:18]([O:31][CH2:32][CH:33]([F:36])[CH2:34]I)([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)([CH3:17])([CH3:16])[CH3:15].C(=O)([O-])[O-].[Cs+].[Cs+].O>CN(C)C=O>[Si:18]([O:31][CH2:32][CH:33]([F:36])[CH2:34][N:8]1[C:9](=[O:12])[CH:10]=[N:11][C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[N:13][C:7]1=2)([C:14]([CH3:16])([CH3:17])[CH3:15])([C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1)[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 10796Cesium carbonateHCID 667398036-Methoxypyrido[2,3-B]pyrazin-3(4H)-oneHCID 86724949Tert-butyl(2-fluoro-3-iodopropoxy)diphenylsilane

Produkt 1

HCID 867249484-(3-{[tert-Butyl(diphenyl)silyl]oxy}-2-fluoropropyl)-6-methoxypyrido[2,3-b]pyrazin-3(4H)-oneAusbeute 67 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

6-Methoxypyrido[2,3-b]pyrazin-3(4H)-one (215 mg, 1.213 mmol) and tert-butyl(2-fluoro-3-iodopropoxy)diphenylsilane (805 mg, 1.820 mmol) were dissolved in N,N-dimethylformamide (6 ml). Cesium carbonate (553 mg, 1.698 mmol) was added to the solution and the mixture was stirred at room temperature for 7 hours. Water was added to the reaction solution and the mixture was extracted with ethyl acetate. The extract was washed with saturated sodium chloride solution, dried over anhydrous sodium sulfate and the solvent was removed under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate) to yield 399 mg (67%) of the title compound in the form of a light orange solid.

Aufarbeitung

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with saturated sodium chloride solution
  3. dry with materialdried over anhydrous sodium sulfate
  4. customthe solvent was removed under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-87ffbf989c784f95b0484ab2232b1939
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08952010B2

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