Ethanol → HCID 178433715, compound

HRID 1736583Notes

Reaction equation

HRID 1736583 reaction equation
C(C1[CH:8]=[CH:7][C:6]([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:5][CH:4]=1)#N.[OH-:27].[Na+].[CH2:29]([OH:31])[CH3:30]>>[C:29]([C:30]1[CH:8]=[CH:7][C:6]([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:5][CH:4]=1)([OH:27])=[O:31]

Participants

4

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 178433713HCID 178433713, compound

Product 1

HCID 178433715HCID 178433715, compoundYield 16%

Procedure

A mixture of 1-(4-cyanophenylmethyl)-3-methyl-6-(4-pyridyl)-pyrazolo[3,4-d]pyrimidin-4-one (1.6 g, 4.5 mmol), 10M NaOH (50 ml) and ethanol (50 ml) was refluxed for 4 hours. The mixture was filtered while hot, the filtrate was cooled and acidified with acetic acid (pH 6). The product was collected by filtration and washed with ethanol and ether. The product was recrystallized from DMF to afford 0.26 g (16%) of 1-(4-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 120° C. for 18 hours in high vacuum.

Workup

  1. temperaturewas refluxed for 4 hours
  2. filtrationThe mixture was filtered while hot, the filtrate
  3. temperaturewas cooled
  4. filtrationThe product was collected by filtration
  5. washwashed with ethanol and ether
  6. customThe product was recrystallized from DMF

Sources & evidence

ORD record
ord-844a8c9364c843c291bf729509441918
Source dataset
uspto-grants-1996_07
Patent number
US05541187

Reaction notes

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