Potassium Carbonate → 7-Benzyl-3-cyclopropylmethyl-1-propoxymethylxanthine

HRID 323865Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 323865
C(=O)([O-])[O-].[K+].[K+].[CH2:7]([N:14]1[C:22]2[C:21](=[O:23])[NH:20][C:19](=[O:24])[N:18]([CH2:25][CH:26]3[CH2:28][CH2:27]3)[C:17]=2[N:16]=[CH:15]1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[CH2:29]([O:32][CH2:33]Cl)[CH2:30][CH3:31]>CN(C)C=O.O.CO>[CH2:7]([N:14]1[C:22]2[C:21](=[O:23])[N:20]([CH2:33][O:32][CH2:29][CH2:30][CH3:31])[C:19](=[O:24])[N:18]([CH2:25][CH:26]3[CH2:28][CH2:27]3)[C:17]=2[N:16]=[CH:15]1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Komponenten

7

Edukt 3

HCID 11430Potassium CarbonateHCID 109644311-(Chloromethoxy)propaneHCID 220073157-Benzyl-3-cyclopropylmethylxanthine

Produkt 1

HCID 220073077-Benzyl-3-cyclopropylmethyl-1-propoxymethylxanthine

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittel2×HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

1.12 g (8.1 mmol) of potassium carbonate were added at 60° C. to a solution of 1.5 g (5.06 mmol) of 7-benzyl-3-cyclopropylmethylxanthine from stage a) in 60 ml of dimethylformamide and the mixture was stirred at this temperature for one hour. 722 μl (6.58 mmol) of propoxymethyl chloride were then added dropwise and the mixture was stirred at 80° C. for 4 hours. 12 ml of water and 5 ml of methanol were added and the mixture was stirred at 50° C. for 2 hours. 60 ml of water were then added again, the mixture was extracted three times using methyl tert-butyl ether, and the combined organic phases were washed twice with water, dried using magnesium sulfate and concentrated under reduced pressure. The crude product was purified by flash chromatography on a silica gel column, dichloromethane/methanol (19.8/0.2).

Aufarbeitung

  1. stirringthe mixture was stirred at 80° C. for 4 hours
  2. stirringthe mixture was stirred at 50° C. for 2 hours
  3. extractionthe mixture was extracted three times
  4. washthe combined organic phases were washed twice with water
  5. customdried
  6. concentrationconcentrated under reduced pressure
  7. customThe crude product was purified by flash chromatography on a silica gel column, dichloromethane/methanol (19.8/0.2)

Quellen und Nachweise

ORD-Eintrag
ord-29c96520b9dd4307bc40135b381bfc09
Quelldatensatz
uspto-grants-2001_04
Patentnummer
US06214992B1

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