Ethanol → HCID 178433712, compound

HRID 1736584Notes

Reaction equation

HRID 1736584 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH2:9][N:10]2[C:14]3=[N:15][C:16]([C:20]4[CH:25]=[CH:24][N:23]=[CH:22][CH:21]=4)=[N:17][C:18](=[O:19])[C:13]3=[C:12]([CH3:26])[NH:11]2)[CH:6]=CC=1)#N.[OH-:27].[Na+].[CH2:29]([OH:31])[CH3:30]>>[C:29]([C:30]1[CH:6]=[C:5]([CH2:9][N:10]2[C:14]3=[N:15][C:16]([C:20]4[CH:25]=[CH:24][N:23]=[CH:22][CH:21]=4)=[N:17][C:18](=[O:19])[C:13]3=[C:12]([CH3:26])[NH:11]2)[CH:4]=[CH:3][CH:1]=1)([OH:27])=[O:31]

Participants

4

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 178433710HCID 178433710, compound

Product 1

HCID 178433712HCID 178433712, compoundYield 25%

Procedure

A mixture of 1-(3-cyanophenylmethyl)-3-methyl-6-(4-pyridyl)-pyrazolo[3,4-d]pyrimidin-4-one (3.4 g, 10.2 mmol), 10 M NaOH (100 ml) and ethanol (100 ml) was refluxed for 7 hours. The mixture was filtered hot, the filtrate was cooled in an ice-bath for 30 minutes and neutralized with acetic acid. The product was collected by filtration and washed with water, ethanol and ether. The solid residue was digested in methanol and the product was collected by filtration and washed with ether. The product was recrystallized from DMF to afford 0.91 g (25%) of 1-(3-carboxyphenylmethyl)3-methyl-6-(4-pyridyl)-pyrazolo[3,4-d]pyrimidin-4-one as an off-white powder, m.p. >300° C. when dried at 125° C. for 18 hours in high vacuum.

Workup

  1. temperaturewas refluxed for 7 hours
  2. filtrationThe mixture was filtered hot
  3. temperaturethe filtrate was cooled in an ice-bath for 30 minutes
  4. filtrationThe product was collected by filtration
  5. washwashed with water, ethanol and ether
  6. filtrationthe product was collected by filtration
  7. washwashed with ether
  8. customThe product was recrystallized from DMF

Sources & evidence

ORD record
ord-8d1acdd8020d42b5b0d1320ca80549c7
Source dataset
uspto-grants-1996_07
Patent number
US05541187

Reaction notes

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