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

HRID 566352Notes

Reaction equation

HRID 566352 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].[Cl:20][C:21]1[CH:22]=[C:23]([CH2:29][C:30](OC)=O)[CH:24]=[CH:25][C:26]=1[O:27][CH3:28].[O-]CC.[Na+].C(=O)([O-])O.[Na+]>ClCCl>[Cl:20][C:21]1[CH:22]=[C:23]([CH:24]=[CH:25][C:26]=1[O:27][CH3:28])[CH2:29][C:30]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 516892Sodium BicarbonateHCID 2723922Sodium ethoxideHCID 12236892Methyl 3-chloro-4-methoxyphenylacetateHCID 599323475-amino-3-methyl-(3-nonyl)-1H-pyrazole-4-carboxamide

Product 1

HCID 1361321486-(3-Chloro-4-methoxy-benzyl)-1-(3-nonyl)-3-methyl-1,5-dihydro-pyrazolo[3,4-d]pyrimidin-4-oneYield 47%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

13 mg (0.050 mmol) of 5-amino-3-methyl-1-(3-nonyl)-1H-pyrazole-4-carboxamide and 53 mg (0.248 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 10.1 mg (47%) of a solid, Rf=0.63 (dichloromethane/methanol=15:1).

Workup

  1. customthe phases are separated
  2. customPurification by chromatography

Sources & evidence

ORD record
ord-ba01a901cb4a413fa43654f09d297cd4
Source dataset
uspto-grants-2001_01
Patent number
US06174884B1

Reaction notes

Loading…