Reacción #2112

ord-7a6debe642dd4a55a17f79ac83e9ef86

Ecuación de reacción

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

Reactantes

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

Reactivos

Ninguno

Disolventes

CN(C)C=O
dimethylformamide

Condiciones de reacción

Temperatura
70°CELSIUS
Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    Filtraciónfiltered
  2. 2
    Concentraciónthe filtrate was concentrated under reduced pressure
  3. 3
    Filtraciónfiltered again
  4. 4
    Otrocrystallized from diisopropyl ether

Procedimiento

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.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US05728686uspto-grants-1998_03