HCID 19432778, compound → HCID 178433720, compound

HRID 487290Notes

Reaction equation

HRID 487290 reaction equation
[CH3:1][N:2]1[C:6]2=[N:7][C:8]([C:12]3[CH:17]=[CH:16][N:15]=[CH:14][CH:13]=3)=[N:9][C:10](N)=[C:5]2[C:4]([CH3:18])=[N:3]1.N([O-])=[O:20].[Na+]>S(=O)(=O)(O)O.O>[CH3:1][N:2]1[C:6]2=[N:7][C:8]([C:12]3[CH:17]=[CH:16][N:15]=[CH:14][CH:13]=3)=[N:9][C:10](=[O:20])[C:5]2=[C:4]([CH3:18])[NH:3]1

Participants

5

Reactant 2

HCID 19432778HCID 19432778, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 178433720HCID 178433720, compoundYield 76%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1118Sulfuric AcidSolvent

Procedure

A solution of 1,3-dimethyl-6-(4-pyridyl)-pyrazolo[3,4-d]-pyrimidin-4-amine (1.99 g, 8.3 mmol) in 50% aqueous sulfuric acid (50 ml) at 0° C. was stirred for 20 minutes and sodium nitrite (5.7 g, 83.0 mmol) in water (25 ml) was added dropwise over 1 hour. The reaction mixture was allowed to warm to room temperature and was stirred for 24 hours. The mixture was poured into ice-water (500 ml) and a white solid was collected by filtration and washed with water, ethanol and finally ether. The solid residue was stirred in 15% KHCO3 (150 ml) for 20 minutes and the product was collected by filtration and washed with water, then ethanol and finally ether. The product was recrystallized from DMF to afford 1.5 g (76%) of 1,3-dimethyl-6-(4-pyridyl)-pyrazolo[3,4-d]-pyrimidin-4-one as a white solid, m.p. >301° C. when dried for 18 hours at 115° C. in high vacuum.

Workup

  1. filtrationa white solid was collected by filtration
  2. washwashed with water, ethanol and finally ether
  3. stirringThe solid residue was stirred in 15% KHCO3 (150 ml) for 20 minutes
  4. filtrationthe product was collected by filtration
  5. washwashed with water
  6. customThe product was recrystallized from DMF

Sources & evidence

ORD record
ord-a7b919280f704afaadb57370440c7be3
Source dataset
uspto-grants-1994_03
Patent number
US05294612

Reaction notes

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