Water → 7-Benzyl-8-(3-oxocyclopentyl)-1,3-dipropylpurine-2,6-dione

HRID 1684521Notes

Reaction equation

HRID 1684521 reaction equation
[O:1]=[C:2]1[CH2:6][CH2:5][CH:4]([C:7]2[NH:15][C:14]3[C:13](=[O:16])[N:12]([CH2:17][CH2:18][CH3:19])[C:11](=[O:20])[N:10]([CH2:21][CH2:22][CH3:23])[C:9]=3[N:8]=2)[CH2:3]1.C(=O)([O-])[O-].[K+].[K+].[CH2:30](Br)[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.O>CN(C)C=O>[CH2:30]([N:15]1[C:14]2[C:13](=[O:16])[N:12]([CH2:17][CH2:18][CH3:19])[C:11](=[O:20])[N:10]([CH2:21][CH2:22][CH3:23])[C:9]=2[N:8]=[C:7]1[CH:4]1[CH2:5][CH2:6][C:2](=[O:1])[CH2:3]1)[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 131584Kfm 19

Product 1

HCID 149891347-Benzyl-8-(3-oxocyclopentyl)-1,3-dipropylpurine-2,6-dione

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

10.0 g (0.031 mol) of 8-(3-oxocyclopentyl)-1,3-dipropyl-7H-purine-2,6-dione are dissolved in 30 ml of absolute dimethylformamide and after the addition of 4.6 g (0.033 mol) of potassium carbonate the mixture is stirred for 20 minutes at ambient temperature. 5.7 g (0.033 mol) of benzylbromide are added dropwise, the mixture is stirred for a further 40 minutes and the reaction is ended by the addition of water. The solution is evaporated down, the residue is taken up in water and extracted with dichloromethane. After drying and evaporation, the combined organic phases yield an oily residue which is purified on silica gel with a mixture of dichloromethane/methanol in the ratio 99:1 and then recrystallised from ethanol. 9.4 g (73.3% of theory) of the title compound are obtained in the form of colourless crystals, melting point: 145° C.

Workup

  1. stirringthe mixture is stirred for a further 40 minutes
  2. customThe solution is evaporated down
  3. extractionextracted with dichloromethane
  4. customAfter drying
  5. customevaporation
  6. customthe combined organic phases yield an oily residue which
  7. customis purified on silica gel with a mixture of dichloromethane/methanol in the ratio 99:1
  8. customrecrystallised from ethanol

Sources & evidence

ORD record
ord-b89fd8ee099c48239e78592246e69cde
Source dataset
uspto-grants-1997_06
Patent number
US05641784

Reaction notes

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