Potassium Carbonate → Diethyl [4-(7-benzyl-3-methylxanthin-1-yl)butyl]phosphonate

HRID 2016

Reaction equation

HRID 2016 reaction equation
[CH2:1]([N:8]1[C:16]2[C:15](=[O:17])[NH:14][C:13](=[O:18])[N:12]([CH3:19])[C:11]=2[N:10]=[CH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[CH2:21][CH2:22][CH2:23][CH2:24][P:25]([O:30][CH2:31][CH3:32])(=[O:29])[O:26][CH2:27][CH3:28].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH2:1]([N:8]1[C:16]2[C:15](=[O:17])[N:14]([CH2:21][CH2:22][CH2:23][CH2:24][P:25](=[O:29])([O:30][CH2:31][CH3:32])[O:26][CH2:27][CH3:28])[C:13](=[O:18])[N:12]([CH3:19])[C:11]=2[N:10]=[CH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 6856307-Benzyl-3-methylxanthineHCID 19689195Diethyl(4-chlorobutyl)phosphonate

Product 1

HCID 22446297Diethyl [4-(7-benzyl-3-methylxanthin-1-yl)butyl]phosphonate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

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.

Workup

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

Sources & evidence

ORD record
ord-7a6debe642dd4a55a17f79ac83e9ef86
Source dataset
uspto-grants-1998_03
Patent number
US05728686

Linked notes

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