Ethyl Acetoacetate → 3-(3,5-dimethoxyphenyl)-1,4-dimethyl-1H-pyrazolo[3,4-b]pyridin-6(7H)-one

HRID 402497Notes

Reaction equation

HRID 402497 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[CH:15]=[C:14]([NH2:16])[N:13]([CH3:17])[N:12]=2)[CH:6]=[C:7]([O:9][CH3:10])[CH:8]=1.C([O:20][C:21](=O)[CH2:22][C:23](=O)[CH3:24])C>C(O)(=O)C>[CH3:10][O:9][C:7]1[CH:6]=[C:5]([C:11]2[C:15]3[C:23]([CH3:24])=[CH:22][C:21](=[O:20])[NH:16][C:14]=3[N:13]([CH3:17])[N:12]=2)[CH:4]=[C:3]([O:2][CH3:1])[CH:8]=1

Participants

4

Reactant 2

HCID 8868Ethyl AcetoacetateHCID 431588653-(3,5-dimethoxyphenyl)-1-methyl-1H-pyrazol-5-amine

Product 1

HCID 1363765163-(3,5-dimethoxyphenyl)-1,4-dimethyl-1H-pyrazolo[3,4-b]pyridin-6(7H)-oneYield 60%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 3-(3,5-dimethoxyphenyl)-1-methyl-1H-pyrazol-5-amine (1.3 g, 5.57 mmol) and 3-oxo-butyric acid ethyl ester (1.09 g, 8.36 mmol) in acetic acid (5 ml) was stirred at 150° C. for 18 h. The solution was evaporated under reduced pressure and the resulting crude product was purified by column chromatography (eluent 10% MeOH in CH2Cl2) to yield 1.0 g (60%) of the title compound. [1H-NMR (DMSO-d6, 360 MHz): δ 6.68 (d, 2H), 6.56 (s, 1H), 6.18 (s, 1H), 3.90 (s, 3H), 3.78 (s, 6H), 2.24 (s, 3H); UPLC-MS RtJ=0.79 min; [M+H]+=300.1]

Workup

  1. customThe solution was evaporated under reduced pressure
  2. customthe resulting crude product was purified by column chromatography (eluent 10% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-afdfb95569a941cb875021bc1d31260e
Source dataset
uspto-grants-2014_06
Patent number
US08742106B2

Reaction notes

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