Sodium Bicarbonate → 6-(3-Ethoxycarbonyl-benzyl)-1-(3-nonyl)-3-methyl-1,5-dihydro-pyrazolo[3,4-d]pyrimidin-4-one

HRID 566351Notes

Reaction equation

HRID 566351 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].[CH2:20]([O:22][C:23]([C:25]1[CH:26]=[C:27]([CH2:31][C:32](OC)=O)[CH:28]=[CH:29][CH:30]=1)=[O:24])[CH3:21].[O-]CC.[Na+].C(=O)([O-])O.[Na+]>ClCCl>[CH2:20]([O:22][C:23]([C:25]1[CH:26]=[C:27]([CH:28]=[CH:29][CH:30]=1)[CH2:31][C:32]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)=[O:24])[CH3:21]

Participants

6

Reactant 4

HCID 516892Sodium BicarbonateHCID 2723922Sodium ethoxideHCID 21266104Methyl 3-ethoxycarbonylphenylacetateHCID 599323475-amino-3-methyl-(3-nonyl)-1H-pyrazole-4-carboxamide

Product 1

HCID 1361321646-(3-Ethoxycarbonyl-benzyl)-1-(3-nonyl)-3-methyl-1,5-dihydro-pyrazolo[3,4-d]pyrimidin-4-oneYield 37%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

11 mg (0.042 mmol) of 5-amino-3-methyl-1-(3-nonyl)-1H-pyrazole-4-carboxamide and 37 mg (0.167 mmol) of methyl 3-ethoxycarbonylphenylacetate 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 6.8 mg (37%) of a solid, Rf=0.47 (dichloromethane/methanol=15:1).

Workup

  1. customthe phases are separated
  2. customPurification by chromatography

Sources & evidence

ORD record
ord-d51f0fe82c7242a48f326a11382d94f0
Source dataset
uspto-grants-2001_01
Patent number
US06174884B1

Reaction notes

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