Potassium Hydroxide → 8-(3-Carboxycyclopentyl)-1,3-dipropyl-7H-purine-2,6-dione

HRID 1684525Notes

Reaction equation

HRID 1684525 reaction equation
C[O:2][C:3]([CH:5]1[CH2:9][CH2:8][CH:7]([C:10]2[NH:18][C:17]3[C:16](=[O:19])[N:15]([CH2:20][CH2:21][CH3:22])[C:14](=[O:23])[N:13]([CH2:24][CH2:25][CH3:26])[C:12]=3[N:11]=2)[CH2:6]1)=[O:4].[OH-].[K+]>C(O)C.O>[C:3]([CH:5]1[CH2:9][CH2:8][CH:7]([C:10]2[NH:18][C:17]3[C:16](=[O:19])[N:15]([CH2:20][CH2:21][CH3:22])[C:14](=[O:23])[N:13]([CH2:24][CH2:25][CH3:26])[C:12]=3[N:11]=2)[CH2:6]1)([OH:4])=[O:2]

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 149891208-(3-methyloxycarbonylcyclopentyl)-1,3-dipropyl-7H-purine-2,6-dione

Product 1

HCID 190398248-(3-Carboxycyclopentyl)-1,3-dipropyl-7H-purine-2,6-dione

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
10 °C

Procedure

1.41 g (3.9 mmol) of 8-(3-methyloxycarbonylcyclopentyl)-1,3-dipropyl-7H-purine-2,6-dione are suspended in 10 ml of ethanol and 1 ml of water, 0.77 g of potassium hydroxide are added and the mixture is refluxed for 30 minutes. After cooling to 10° C. the mixture is acidified, the crystals precipitated are suction filtered and the filtrate is extracted with dichloromethane. The combined organic extracts are dried and evaporated down; the residue is combined with the filtered crystals. In this way 1.27 g (93.4% of theory) of the title compound are obtained are beige crystals.

Workup

  1. temperaturethe mixture is refluxed for 30 minutes
  2. customthe crystals precipitated
  3. filtrationare suction filtered
  4. extractionthe filtrate is extracted with dichloromethane
  5. customThe combined organic extracts are dried
  6. customevaporated down

Sources & evidence

ORD record
ord-4a67d5f5304f4a64b00a1c0d817d3d73
Source dataset
uspto-grants-1997_06
Patent number
US05641784

Reaction notes

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