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

HRID 566354Notes

Reaction equation

HRID 566354 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]([CH2:16][CH3:17])[C:3]=1[C:18]([NH2:20])=[O:19].[Cl: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>[Cl: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:20][C:18](=[O:19])[C:3]2[C:4]([CH2:16][CH3:17])=[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 516892Sodium BicarbonateHCID 2723922Sodium ethoxideHCID 12236892Methyl 3-chloro-4-methoxyphenylacetateHCID 599323285-amino-3-ethyl-1-(3-nonyl)-1H-pyrazole-4-carboxamide

Product 1

HCID 1363863786-(3-Chloro-4-methoxy-benzyl)-1-(3-nonyl)-3-ethyl-1,5-dihydro-pyrazolo[3,4-d]pyrimidin-4-oneYield 28%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

18 mg (0.065 mmol) of 5-amino-3-ethyl-1-(3-nonyl)-1H-pyrazole-4-carboxamide and 69 mg (0.323 mmol) of methyl 3-chloro-4-methoxyphenylacetate 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 8 mg (28%) of a solid, Rf=0.75 (dichloromethane/methanol=15:1).

Workup

  1. customthe phases are separated
  2. customPurification by chromatography

Sources & evidence

ORD record
ord-23c30ba48fd2465184082bc00b8b62cb
Source dataset
uspto-grants-2001_01
Patent number
US06174884B1

Reaction notes

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