Reaktion #2112

ord-7a6debe642dd4a55a17f79ac83e9ef86

Reaktionsgleichung

Cn1c(=O)[nH]c(=O)c2c1ncn2Cc1ccccc1
7-benzyl-3-methylxanthine
CCOP(=O)(CCCCCl)OCC
diethyl 4-chlorobutanephosphonate
O=C([O-])[O-].[K+].[K+]
potassium carbonate
→
CCOP(=O)(CCCCn1c(=O)c2c(ncn2Cc2ccccc2)n(C)c1=O)OCC
Diethyl [4-(7-benzyl-3-methylxanthin-1-yl)butyl]phosphonate

Edukte

Cn1c(=O)[nH]c(=O)c2c1ncn2Cc1ccccc1
7-benzyl-3-methylxanthine
CCOP(=O)(CCCCCl)OCC
diethyl 4-chlorobutanephosphonate
O=C([O-])[O-].[K+].[K+]
potassium carbonate

Reagenzien

Keine

Lösungsmittel

CN(C)C=O
dimethylformamide

Reaktionsbedingungen

Temperatur
70°CELSIUS
Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Filtrationfiltered
  2. 2
    Einengenthe filtrate was concentrated under reduced pressure
  3. 3
    Filtrationfiltered again
  4. 4
    Sonstigecrystallized from diisopropyl ether

Vorschrift

20.4 g (0.08 mol) of 7-benzyl-3-methylxanthine were suspended in 200 ml of dimethylformamide (DMF), treated with 22 g (0.96 mol) of diethyl 4-chlorobutanephosphonate and 13.8 g (0.1 mol) of activated potassium carbonate and heated at 70° C. for 4 hours and filtered, the filtrate was concentrated under reduced pressure and the oily residue which remained was taken up in ethyl acetate, filtered again and crystallized from diisopropyl ether.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US05728686uspto-grants-1998_03