Diphenyl Ether → 2-Methyl-2,7-dihydro-pyrazolo[3,4-b]pyridin-4-one

HRID 607153Notes

Reaction equation

HRID 607153 reaction equation
CC1(C)O[C:6](=[O:8])[C:5](=[CH:9][NH:10][C:11]2[CH:15]=[CH:14][N:13]([CH3:16])[N:12]=2)C(=O)O1.C1(OC2C=CC=CC=2)C=CC=CC=1>CC(C)=O>[CH3:16][N:13]1[CH:14]=[C:15]2[C:11]([NH:10][CH:9]=[CH:5][C:6]2=[O:8])=[N:12]1

Participants

4

Reactant 2

HCID 7583Diphenyl EtherHCID 670477842,2-Dimethyl-5-[(1-methyl-1H-pyrazol-3-ylamino)-methylene]-[1,3]dioxane-4,6-dione

Product 1

HCID 1364007322-Methyl-2,7-dihydro-pyrazolo[3,4-b]pyridin-4-oneYield 40.4%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of the product of Example 8a (1.50 g, 5.97 mmol) and diphenyl ether (25 mL) was heated under reflux for 1 h, with removal of the resultant acetone by distillation. The solvent was then decanted, and the remaining solid residue was dissolved in dichloromethane (5 mL) and purified by chromatography on silica gel, eluting with a 0-10% MeOH/CH2Cl2 gradient, to provide the title compound (0.360 g, 40% yield).

Workup

  1. temperaturewas heated
  2. customThe solvent was then decanted
  3. dissolutionthe remaining solid residue was dissolved in dichloromethane (5 mL)
  4. custompurified by chromatography on silica gel
  5. washeluting with a 0-10% MeOH/CH2Cl2 gradient

Sources & evidence

ORD record
ord-c61d5a4d2d814c71b860c69af59a3f66
Source dataset
uspto-grants-2011_03
Patent number
US07915411B2

Reaction notes

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