Sodium hydride → HCID 54432354, Verbindung

HRID 1835728

Reaktionsgleichung

Reaktionsgleichung von HRID 1835728
[H-].[Na+].[Br:3][C:4]1[N:12]([CH3:13])[C:11]2[C:10](=[O:14])[NH:9][C:8](=[O:15])[N:7]([CH3:16])[C:6]=2[N:5]=1.[C:17]([O:20][CH:21]([CH3:33])[CH2:22][CH2:23][CH2:24][CH2:25][C@H](Cl)CCCCC)(=[O:19])[CH3:18]>CS(C)=O>[C:17]([O:20][C@H:21]([CH3:33])[CH2:22][CH2:23][CH2:24][CH2:25][N:9]1[C:10](=[O:14])[C:11]2[N:12]([CH3:13])[C:4]([Br:3])=[N:5][C:6]=2[N:7]([CH3:16])[C:8]1=[O:15])(=[O:19])[CH3:18]

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 7022428-Bromo-3,7-dimethyl-3,7-dihydro-1H-purine-2,6-dioneHCID 86584512HCID 86584512, Verbindung

Produkt 1

HCID 54432354HCID 54432354, VerbindungAusbeute 74 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Versuchsvorschrift

To a stirring suspension of sodium hydride (740 mg, 30.8 mmol) in anhydrous dimethylsulfoxide (120 ml) was added 8-bromo-3,7-dimethylxanthine (6.5 g, 25.0 mmol). After stirring at room temperature under argon for 1.5 hours, (R)-5-acetoxyhexyl-1-chlorohexane (4.91 g, 27.5 mmol) was added and the mixture was stirred at 80° C. for 18 hours. After cooling to room temperature, the reaction mixture was quenched by addition of saturated aqueous sodium chloride solution (300 ml) and extracted with ethyl acetate (3×50 ml). The combined extracts were washed with water (2×20 ml), with saturated aqueous sodium chloride solution (20 ml) and dried over magnesium sulfate. After evaporation of the solvent under reduced pressure, the crude product was purified by flash chromatography on silica gel eluting with ethyl acetate-hexane (1:1) to provide (R)-1-(5-acetoxyhexyl)-8-bromo-3,7-dimethylxanthine (7.38 g, 74% yield) as a colorless oil.

Aufarbeitung

  1. stirringthe mixture was stirred at 80° C. for 18 hours
  2. temperatureAfter cooling to room temperature
  3. customthe reaction mixture was quenched by addition of saturated aqueous sodium chloride solution (300 ml)
  4. extractionextracted with ethyl acetate (3×50 ml)
  5. washThe combined extracts were washed with water (2×20 ml), with saturated aqueous sodium chloride solution (20 ml)
  6. dry with materialdried over magnesium sulfate
  7. customAfter evaporation of the solvent under reduced pressure
  8. customthe crude product was purified by flash chromatography on silica gel eluting with ethyl acetate-hexane (1:1)

Quellen und Nachweise

ORD-Eintrag
ord-9afeedc4dc6c4fef8cfb30d24d794437
Quelldatensatz
uspto-grants-2004_08
Patentnummer
US06774130B2

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