Iodoethane → Diethyl [4-(7-ethyl-3-methylxanthin-1-yl)butyl]phosphonate

HRID 2023

Reaction equation

HRID 2023 reaction equation
[CH3:1][N:2]1[C:10]2[N:9]=[CH:8][NH:7][C:6]=2[C:5](=[O:11])[N:4]([CH2:12][CH2:13][CH2:14][CH2:15][P:16](=[O:23])([O:20][CH2:21][CH3:22])[O:17][CH2:18][CH3:19])[C:3]1=[O:24].[CH2:25](I)[CH3:26].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH2:25]([N:7]1[C:6]2[C:5](=[O:11])[N:4]([CH2:12][CH2:13][CH2:14][CH2:15][P:16](=[O:23])([O:17][CH2:18][CH3:19])[O:20][CH2:21][CH3:22])[C:3](=[O:24])[N:2]([CH3:1])[C:10]=2[N:9]=[CH:8]1)[CH3:26]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 22446315Diethyl [4-(3-methylxanthin-1-yl)butyl]phosphonate

Product 1

HCID 22446294Diethyl [4-(7-ethyl-3-methylxanthin-1-yl)butyl]phosphonate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

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.

Workup

  1. filtrationThe solid was filtered off
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. filtrationfiltered again
  4. customcrystallized from diisopropyl ether

Sources & evidence

ORD record
ord-056956b73b9f45e9955998f708e34b9b
Source dataset
uspto-grants-1998_03
Patent number
US05728686

Linked notes

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