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

HRID 1990Notes

Reaction equation

HRID 1990 reaction equation
Cl.[CH2:2]([N:9]1[C:18](=[O:19])[C:17]2[NH:16][CH:15]=[N:14][C:13]=2[N:12]([CH3:20])[C:10]1=[O:11])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.Cl[CH2:22][CH2:23][CH2:24][CH2:25][P:26]([O:31][CH2:32][CH3:33])(=[O:30])[O:27][CH2:28][CH3:29].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH2:2]([N:9]1[C:18](=[O:19])[C:17]2[N:16]([CH2:22][CH2:23][CH2:24][CH2:25][P:26](=[O:30])([O:31][CH2:32][CH3:33])[O:27][CH2:28][CH3:29])[CH:15]=[N:14][C:13]=2[N:12]([CH3:20])[C:10]1=[O:11])[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 19689195Diethyl(4-chlorobutyl)phosphonateHCID 19689240HCID 19689240, compound

Product 1

HCID 22446290Diethyl [4-(1-benzyl-3-methylxanthin-7-yl)butyl]phosphonate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

20 g (0.078 mol) of 1-benzyl-3-methylxanthine hydrochloride, 21.4 g (0.094 mol) of diethyl 4-chlorobutanephosphonate and 26 g (0.2 mol) of potassium carbonate were suspended in 400 ml of dimethylformamide and stirred at 70° C. for 6 hours. The solution was filtered hot and the dimethylformamide was evaporated under reduced pressure. The oily residue which remained was taken up in dichloromethane and washed several times with water. After evaporating the solvent, it was possible to reuse the pale yellow, oily residue without purification.

Workup

  1. filtrationThe solution was filtered hot
  2. customthe dimethylformamide was evaporated under reduced pressure
  3. washwashed several times with water
  4. customAfter evaporating the solvent, it
  5. customwithout purification

Sources & evidence

ORD record
ord-1b88eb8cb6094a9a8d87846b4529cb21
Source dataset
uspto-grants-1998_03
Patent number
US05728686

Reaction notes

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