Water → 1-(5-Hexenyl)-3-methyl-7-(methylpivaloyl)xanthine

HRID 361481Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 361481
[H-].[Na+].[CH3:3][N:4]1[C:12]2[N:11]=[CH:10][N:9]([C:13](=[O:19])[C:14]([CH3:18])([CH3:17])[CH2:15][CH3:16])[C:8]=2[C:7](=[O:20])[NH:6][C:5]1=[O:21].Br[CH2:23][CH2:24][CH2:25][CH2:26][CH:27]=[CH2:28].O>CS(C)=O.C(OCC)(=O)C>[CH2:28]([N:6]1[C:7](=[O:20])[C:8]2[N:9]([C:13](=[O:19])[C:14]([CH3:17])([CH3:18])[CH2:15][CH3:16])[CH:10]=[N:11][C:12]=2[N:4]([CH3:3])[C:5]1=[O:21])[CH2:27][CH2:26][CH2:25][CH:24]=[CH2:23]

Komponenten

7

Edukt 4

HCID 962WaterHCID 24758Sodium hydrideHCID 759066-Bromo-1-hexeneHCID 215842333-Methyl-7-(methylpivaloyl)xanthine

Produkt 1

HCID 232959671-(5-Hexenyl)-3-methyl-7-(methylpivaloyl)xanthineAusbeute 69,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679Dimethyl SulfoxideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Sodium hydride (86 mg, 3.6 mmol) was added to a stirring solution of 3-methyl-7-(methylpivaloyl)xanthine 1404 (1.00 g, 3.6 mmol) in dimethyl sulfoxide (25 mL). After 15 minutes, 6-bromo-1-hexene (589 mg, 3.6 mmol) was added and stirring continued for 72 hours. The reaction mixture was then poured into water (70 mL) and extracted with dichloromethane (2×100 mL) and 20% ethanol/dichloromethane (1×100 mL). The combined organic layers were washed with saturated aqueous sodium chloride solution (50 mL) and dried over magnesium sulfate. The solvent was evaporated under vacuum to give a thick oil. Chromotograpy of the resulting thick oil using silica and ethyl acetate yielded 870 mg (67% yield) 1-(5-hexenyl)-3-methyl-7-(methylpivaloyl)xanthine (inventive compound no. 1441)

Aufarbeitung

  1. waitcontinued for 72 hours
  2. extractionextracted with dichloromethane (2×100 mL) and 20% ethanol/dichloromethane (1×100 mL)
  3. washThe combined organic layers were washed with saturated aqueous sodium chloride solution (50 mL)
  4. dry with materialdried over magnesium sulfate
  5. customThe solvent was evaporated under vacuum
  6. customto give a thick oil

Quellen und Nachweise

ORD-Eintrag
ord-1555843c19644351af217eddaad184c4
Quelldatensatz
uspto-grants-1999_02
Patentnummer
US05866576

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