Water → HCID 178437848, compound

HRID 619165Notes

Reaction equation

HRID 619165 reaction equation
[CH:1]1([N:6]2[C:10]3=[N:11][C:12]([C:16]4[CH:21]=[CH:20][CH:19]=[C:18]([O:22][CH2:23][C:24]([O:26]CC)=[O:25])[CH:17]=4)=[N:13][C:14](=[O:15])[C:9]3=[C:8]([CH2:29][CH3:30])[NH:7]2)[CH2:5][CH2:4][CH2:3][CH2:2]1.O.[OH-].[K+]>C(O)C>[CH:1]1([N:6]2[C:10]3=[N:11][C:12]([C:16]4[CH:21]=[CH:20][CH:19]=[C:18]([O:22][CH2:23][C:24]([OH:26])=[O:25])[CH:17]=4)=[N:13][C:14](=[O:15])[C:9]3=[C:8]([CH2:29][CH3:30])[NH:7]2)[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

5

Reactant 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 178472964HCID 178472964, compound

Product 1

HCID 178437848HCID 178437848, compoundYield 85.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a slurry of 1-cyclopentyl-3-ethyl-6-[3-(ethoxycarbonylmethoxy)phenyl]pyrazolo[3,4-d]pyrimidin-4-one (1.23 g, 3.0 mmol) in ethanol (10 ml) was added water (100 ml), followed by 85% KOH (0.4 g). The reaction mixture was heated on a steam bath for 3 hours, cooled to room temperature and filtered. The filtrate was chilled and acidified with acetic acid to afford a white precipitate, which was collected by filtration and washed with water, then ethanol, and finally ether. The product was combined with the product from another experimental run and then was recrystallized from DMF/CH3CN to afford 0.98 g of 1-cyclopentyl-3-ethyl-6-[3-(carboxymethoxy)phenyl]pyrazolo[3,4-d]pyrimidin-4-one, m.p. 299-300° C.

Workup

  1. temperatureThe reaction mixture was heated on a steam bath for 3 hours
  2. filtrationfiltered
  3. temperatureThe filtrate was chilled
  4. customto afford a white precipitate, which
  5. filtrationwas collected by filtration
  6. washwashed with water
  7. customwas recrystallized from DMF/CH3CN

Sources & evidence

ORD record
ord-0df9715199e04c289c239f14907f1131
Source dataset
uspto-grants-1999_09
Patent number
US05958929

Reaction notes

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