Reaction #2119

ord-056956b73b9f45e9955998f708e34b9b

Reaction equation

CCOP(=O)(CCCCn1c(=O)c2[nH]cnc2n(C)c1=O)OCC
diethyl [4-(3-methylxanthin-1-yl)-butyl]phosphonate
CCI
ethyl iodide
O=C([O-])[O-].[K+].[K+]
potassium carbonate
→
CCOP(=O)(CCCCn1c(=O)c2c(ncn2CC)n(C)c1=O)OCC
Diethyl [4-(7-ethyl-3-methylxanthin-1-yl)butyl]phosphonate

Reactants

CCOP(=O)(CCCCn1c(=O)c2[nH]cnc2n(C)c1=O)OCC
diethyl [4-(3-methylxanthin-1-yl)-butyl]phosphonate
CCI
ethyl iodide
O=C([O-])[O-].[K+].[K+]
potassium carbonate

Reagents

None

Solvents

CN(C)C=O
DMF

Conditions

Temperature
60°CELSIUS
Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    FiltrationThe solid was filtered off
  2. 2
    Concentrationthe filtrate was concentrated under reduced pressure
  3. 3
    Filtrationfiltered again
  4. 4
    Othercrystallized from diisopropyl ether

Procedure

7.2 g (0.02 mol) of diethyl [4-(3-methylxanthin-1-yl)-butyl]phosphonate were suspended in 100 ml of DMF, treated with 4.7 g (0.03 mol) of ethyl iodide and 4.1 g (0.03 mol) of activated potassium carbonate and heated at 60° C. for 4 hours. The solid was filtered off, 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.

Source

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