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

HRID 566350Notes

Reaction equation

HRID 566350 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].[NH2:20][C:21]1[CH:26]=[CH:25][C:24]([CH2:27][C:28](OC)=O)=[CH:23][CH:22]=1.[O-]CC.[Na+].C(=O)([O-])O.[Na+]>ClCCl>[NH2:20][C:21]1[CH:26]=[CH:25][C:24]([CH2:27][C:28]2[NH:19][C:17](=[O:18])[C:3]3[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]=3[N:1]=2)=[CH:23][CH:22]=1

Participants

6

Reactant 4

HCID 516892Sodium BicarbonateHCID 2723922Sodium ethoxideHCID 2761030Methyl 2-(4-aminophenyl)acetateHCID 599323475-amino-3-methyl-(3-nonyl)-1H-pyrazole-4-carboxamide

Product 1

HCID 1361321556-(4-Amino-benzyl)-1-(3-nonyl)-3-methyl-1,5-dihydro-pyrazolo[3,4-d]pyrimidin-4-oneYield 35%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

10 mg (0.037 mmol) of 5-amino-3-methyl-1-(3-nonyl)-1H-pyrazole-4-carboxamide and 45 mg (0.274 mmol) of methyl 4-aminophenylacetate 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 4.9 mg (35%) of a solid, Rf=0.45 (dichloromethane/methanol=15:1).

Workup

  1. customthe phases are separated
  2. customPurification by chromatography

Sources & evidence

ORD record
ord-0228b4d25a584d9487a2bc809cb0f204
Source dataset
uspto-grants-2001_01
Patent number
US06174884B1

Reaction notes

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