Benzeneacetic acid, 3,4-dimethoxy-, methyl ester → 6-(3,4-Dimethoxy-benzyl)-1-(3-nonyl)-3-methyl-1,5-dihydro-pyrazolo[3,4-d]pyrimidin-4-one

HRID 566348

Reaction equation

HRID 566348 reaction equation
[NH2:1][C:2]1[N:6]([CH:7]([CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15])[CH2:8][CH3:9])[N:5]=[C:4]([CH3:16])[C:3]=1[C:17]([NH2:19])=[O:18].[CH3:20][O:21][C:22]1[CH:23]=[C:24]([CH2:30][C:31](OC)=O)[CH:25]=[CH:26][C:27]=1[O:28][CH3:29].[O-]CC.[Na+].C(=O)([O-])O.[Na+]>ClCCl>[CH3:20][O:21][C:22]1[CH:23]=[C:24]([CH:25]=[CH:26][C:27]=1[O:28][CH3:29])[CH2:30][C:31]1[NH:19][C:17](=[O:18])[C:3]2[C:4]([CH3:16])=[N:5][N:6]([CH:7]([CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15])[CH2:8][CH3:9])[C:2]=2[N:1]=1

Participants

6

Reactant 4

HCID 85213Benzeneacetic acid, 3,4-dimethoxy-, methyl esterHCID 516892Sodium BicarbonateHCID 2723922Sodium ethoxideHCID 59932347HCID 59932347, compound

Product 1

HCID 1361321566-(3,4-Dimethoxy-benzyl)-1-(3-nonyl)-3-methyl-1,5-dihydro-pyrazolo[3,4-d]pyrimidin-4-oneYield 48%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

10 mg (0.036 mmol) of 5-amino-3-methyl-(3-nonyl)-1H-pyrazole-4-carboxamide and 57 mg (0.274 mmol) of methyl 3,4-dimethoxyphenylacetate are refluxed for 6 hours in 0.5 ml of a 0.5M ethanolic sodium ethoxide solution. After dichloromethane and saturated aqueous sodium hydrogen carbonate solution have been added, the phases are separated. Purification by chromatography gives 7.3 mg (48%) of a solid, Rf=0.57 (dichloromethane/methanol=15:1).

Workup

  1. customthe phases are separated
  2. customPurification by chromatography

Sources & evidence

ORD record
ord-d1a64a1cd3d14eaca0c645f9927cdb7a
Source dataset
uspto-grants-2001_01
Patent number
US06174884B1

Linked notes

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