Hydrogen Peroxide → HCID 178433714, compound

HRID 1736582Notes

Reaction equation

HRID 1736582 reaction equation
[OH-:1].[K+].[C:3]([C:5]1[CH:10]=[CH:9][C:8]([CH2:11][N:12]2[C:16]3=[N:17][C:18]([C:22]4[CH:27]=[CH:26][N:25]=[CH:24][CH:23]=4)=[N:19][C:20](=[O:21])[C:15]3=[C:14]([CH3:28])[NH:13]2)=[CH:7][CH:6]=1)#[N:4].OO>O>[C:3]([C:5]1[CH:6]=[CH:7][C:8]([CH2:11][N:12]2[C:16]3=[N:17][C:18]([C:22]4[CH:27]=[CH:26][N:25]=[CH:24][CH:23]=4)=[N:19][C:20](=[O:21])[C:15]3=[C:14]([CH3:28])[NH:13]2)=[CH:9][CH:10]=1)(=[O:1])[NH2:4]

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 14797Potassium HydroxideHCID 178433713HCID 178433713, compound

Product 1

HCID 178433714HCID 178433714, compoundYield 46.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of potassium hydroxide (0.24 g, 3.7 mmol) in water (10 ml) was stirred in an ice-bath for 30 minutes and 1-(4-cyanophenylmethyl)-3-methyl-6-(4-pyridyl)-pyrazolo[3,4-d]-pyrimidin-4-one (0.42 g, 1.2 mmol) was added, followed by 30% hydrogen peroxide (0.6 ml, 6.1 mmol). The reaction mixture was stirred for 4 hours, warmed to room temperature and stirred for 24 hours. The reaction mixture was filtered, and the filtrate was neutralized with acetic acid to afford a white precipitate. The product was collected by filtration and washed with water, ethanol and ether. The product was recrystallized in DMF to afford 0.2 g (46%) of 1-(4-carbamoylphenylmethyl)-3-methyl-6-(4-pyridyl)-pyrazolo[3,4-d]pyrimidin-4-one as a fluffy white powder, m.p. >300° C. when dried at 120° C. for 24 hours in high vacuum.

Workup

  1. stirringstirred for 24 hours
  2. filtrationThe reaction mixture was filtered
  3. customto afford a white precipitate
  4. filtrationThe product was collected by filtration
  5. washwashed with water, ethanol and ether
  6. customThe product was recrystallized in DMF

Sources & evidence

ORD record
ord-101edc9ef7f240cd8828ac4d7b17da3d
Source dataset
uspto-grants-1996_07
Patent number
US05541187

Reaction notes

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