7-Benzyl-8-(3-methyloxycarbonyl-cyclopentyl)-1,3-dipropylpurine-2,6-dione → 8-(3-methyloxycarbonylcyclopentyl)-1,3-dipropyl-7H-purine-2,6-dione

HRID 1684524Notes

Reaction equation

HRID 1684524 reaction equation
C([N:8]1[C:16]2[C:15](=[O:17])[N:14]([CH2:18][CH2:19][CH3:20])[C:13](=[O:21])[N:12]([CH2:22][CH2:23][CH3:24])[C:11]=2[N:10]=[C:9]1[CH:25]1[CH2:29][CH2:28][CH:27]([C:30]([O:32][CH3:33])=[O:31])[CH2:26]1)C1C=CC=CC=1.[H][H]>CO.[OH-].[OH-].[Pd+2]>[CH3:33][O:32][C:30]([CH:27]1[CH2:28][CH2:29][CH:25]([C:9]2[NH:8][C:16]3[C:15](=[O:17])[N:14]([CH2:18][CH2:19][CH3:20])[C:13](=[O:21])[N:12]([CH2:22][CH2:23][CH3:24])[C:11]=3[N:10]=2)[CH2:26]1)=[O:31]

Participants

5

Reactant 2

HCID 190398367-Benzyl-8-(3-methyloxycarbonyl-cyclopentyl)-1,3-dipropylpurine-2,6-dioneHCID 178418361HCID 178418361, compound

Product 1

HCID 149891208-(3-methyloxycarbonylcyclopentyl)-1,3-dipropyl-7H-purine-2,6-dione

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

2.29 g (5.1 mmol) of 7-benzyl-8-(3-methyloxycarbonyl-cyclopentyl)-1,3-dipropylpurine-2,6-dione are hydrogenated in 40 ml of methanol with the addition of 0.5 g of dry Pearlman catalyst until the uptake of hydrogen has ceased at 20° C. under 5.0 bars. After filtering over kieselguhr the solution is evaporated down and the residue is recrystallised from isopropanol. 1.54 g (83.2% of theory) of the title compound are obtained in the form of colourless crystals, melting point 188°-194° C.

Workup

  1. customhas ceased at 20° C. under 5.0 bars
  2. filtrationAfter filtering over kieselguhr the solution
  3. customis evaporated down
  4. customthe residue is recrystallised from isopropanol

Sources & evidence

ORD record
ord-f3b5c48bf3294239a6af9eab0076da7b
Source dataset
uspto-grants-1997_06
Patent number
US05641784

Reaction notes

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