Acetic Acid → HCID 178433711, compound

HRID 1736585Notes

Reaction equation

HRID 1736585 reaction equation
[OH-].[K+].[C:3]([C:5]1[CH:6]=[C:7]([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:8]=[CH:9][CH:10]=1)#[N:4].OO.C(O)(=[O:33])C>O>[C:3]([C:5]1[CH:6]=[C:7]([CH2:11][N:12]2[C:16]3=[N:17][C:18]([C:22]4[CH:23]=[CH:24][N:25]=[CH:26][CH:27]=4)=[N:19][C:20](=[O:21])[C:15]3=[C:14]([CH3:28])[NH:13]2)[CH:8]=[CH:9][CH:10]=1)(=[O:33])[NH2:4]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 784Hydrogen PeroxideHCID 14797Potassium HydroxideHCID 178433710HCID 178433710, compound

Product 1

HCID 178433711HCID 178433711, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of potassium hydroxide (0.7 g, 9.9 mmol) in water (75 ml) was stirred in an ice-bath for 30 minutes and 1-(3-cyanophenylmethyl)-3-methyl-6-(4-pyridyl)-pyrazolo[3,4-d]-pyrimidin-4-one (1.1 g, 3.3 mmol), followed by 30% hydrogen peroxide (1.7 ml, 16.5 mmol) were added. The mixture was slowly warmed to room temperature and stirred for 24 hours. The mixture was chilled in an ice-bath and neutralized with acetic acid. The product was collected by filtration and washed with water, ethanol and ether. The product was recrystallized from DMF to afford 0.87 g (73%) of 1-(3-carbamoylphenylmethyl)-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 24 hours in high vacuum.

Workup

  1. additionwere added
  2. stirringstirred for 24 hours
  3. temperatureThe mixture was chilled in an ice-bath
  4. filtrationThe product was collected by filtration
  5. washwashed with water, ethanol and ether
  6. customThe product was recrystallized from DMF

Sources & evidence

ORD record
ord-80c4d86f291b4c2e97b1c75690639bf9
Source dataset
uspto-grants-1996_07
Patent number
US05541187

Reaction notes

Loading…