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

HRID 1994Notes

Reaction equation

HRID 1994 reaction equation
[CH2:1]([N:3]1[C:12](=[O:13])[C:11]2[NH:10][CH:9]=[N:8][C:7]=2[N:6]([CH3:14])[C:4]1=[O:5])[CH3:2].Cl[CH:16]([P:20]([O:25][CH2:26][CH3:27])(=[O:24])[O:21][CH2:22][CH3:23])[CH2:17][CH2:18][CH3:19].C(=O)([O-])[O-].[K+].[K+]>>[CH2:1]([N:3]1[C:12](=[O:13])[C:11]2[N:10]([CH2:19][CH2:18][CH2:17][CH2:16][P:20](=[O:24])([O:25][CH2:26][CH3:27])[O:21][CH2:22][CH3:23])[CH:9]=[N:8][C:7]=2[N:6]([CH3:14])[C:4]1=[O:5])[CH3:2]

Participants

4

Reactant 3

HCID 11430Potassium CarbonateHCID 129053881-Ethyl-3-methyl-3,7-dihydro-purine-2,6-dioneHCID 14665078Diethyl chlorobutanephosphonate

Product 1

HCID 22446307Diethyl [4-(1-ethyl-3-methylxanthin-7-yl)butyl]phosphonate

Procedure

9.7 g (0.05 mol) of 1-ethyl-3-methylxanthine were stirred at 70° C. for 6 hours with 12.7 g (0.06 mol) of diethyl chlorobutanephosphonate and 8.3 g of potassium carbonate. The solution was filtered, the solvent was evaporated, and the residue which remained was chromatographed (eluent: ethyl acetate/methanol 10: 1) and crystallized from ethyl acetate/diisopropyl ether.

Workup

  1. filtrationThe solution was filtered
  2. customthe solvent was evaporated
  3. customthe residue which remained was chromatographed (eluent: ethyl acetate/methanol 10: 1)
  4. customcrystallized from ethyl acetate/diisopropyl ether

Sources & evidence

ORD record
ord-66898f10be454898bdbc10dabbccc95a
Source dataset
uspto-grants-1998_03
Patent number
US05728686

Reaction notes

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