Water → HCID 178437838, compound

HRID 619156Notes

Reaction equation

HRID 619156 reaction equation
[CH:1]1([N:6]2[C:10]3=[N:11][C:12]([C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=4[O:22][CH2:23][C:24]([O:26]CC)=[O:25])=[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.C([O-])([O-])=O.[K+].[K+].O>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]=[CH:18][C:17]=4[O:22][CH2:23][C:24]([OH:26])=[O:25])=[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 11430Potassium CarbonateHCID 178472962HCID 178472962, compound

Product 1

HCID 178437838HCID 178437838, compoundYield 74.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 1-cyclopentyl-3-ethyl-6-[2-(ethoxycarbonylmethoxy)pheny]pyrazolo[3,4-d]pyrimidin-4-one (3.0 g, 7.3 mmol), K2CO3 (3.04 g), water (20 ml) and ethanol (50 ml) was refluxed for 1.5 hours. The reaction mixture was cooled, the solvent was removed in vacuo and the residue was slurried with water and acidified. A precipitate formed which was collected by filtration, recrystallized from isopropanol and dried at 90° C. The solid was dissolved in 10% K2CO3 (100 ml), treated with DARCO®, filtered and the filtrate was acidified with acetic acid. A precipitate formed which was collected by filtration and dried at 110° C. The solid product was combined with the solid product obtained from a similar experimental run, stirred with 6N HCL (100 ml), filtered and dried with P2O5 at 100° C. under vacuum to afford 2.09 g of 1-cyclopentyl-3-ethyl-6-[2-(carboxymethoxy)phenyl]pyrazolo[3,4-d]pyrimidin-4-one 1/2 hydrate, m.p. 208-209° C.

Workup

  1. temperaturewas refluxed for 1.5 hours
  2. temperatureThe reaction mixture was cooled
  3. customthe solvent was removed in vacuo
  4. customA precipitate formed which
  5. filtrationwas collected by filtration
  6. customrecrystallized from isopropanol
  7. customdried at 90° C
  8. dissolutionThe solid was dissolved in 10% K2CO3 (100 ml)
  9. additiontreated with DARCO®
  10. filtrationfiltered
  11. customA precipitate formed which
  12. filtrationwas collected by filtration
  13. customdried at 110° C
  14. customobtained from a similar experimental run
  15. filtrationfiltered
  16. dry with materialdried with P2O5 at 100° C. under vacuum

Sources & evidence

ORD record
ord-4799abf0d1da463f87cf708fb1d78b33
Source dataset
uspto-grants-1999_09
Patent number
US05958929

Reaction notes

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