Methyl 2-(1,3-dioxaindan-5-yl)acetate → 6-(3,4-Methylenedioxy-benzyl)-1-(3-nonyl)-3-ethyl-1,5-dihydro-pyrazolo[3,4-d]pyrimidin-4-one

HRID 566353Notes

Reaction equation

HRID 566353 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].[CH2:21]1[O:29][C:28]2[CH:27]=[CH:26][C:25]([CH2:30][C:31](OC)=O)=[CH:24][C:23]=2[O:22]1.CC(C)([O-])C.[K+].C(=O)([O-])O.[Na+]>ClCCl>[CH2:21]1[O:29][C:28]2[CH:27]=[CH:26][C:25]([CH2:30][C:31]3[NH:20][C:18](=[O:19])[C:3]4[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]=4[N:1]=3)=[CH:24][C:23]=2[O:22]1

Participants

6

Reactant 4

HCID 266588Methyl 2-(1,3-dioxaindan-5-yl)acetateHCID 516892Sodium BicarbonateHCID 23665647Potassium tert-butoxideHCID 599323285-amino-3-ethyl-1-(3-nonyl)-1H-pyrazole-4-carboxamide

Product 1

HCID 1361321516-(3,4-Methylenedioxy-benzyl)-1-(3-nonyl)-3-ethyl-1,5-dihydro-pyrazolo[3,4-d]pyrimidin-4-oneYield 12.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

10 mg (0.037 mmol) of 5-amino-3-ethyl-1-(3-nonyl)-1H-pyrazole-4-carboxamide and 30 mg (0.129 mmol) of methyl 3,4-methylenedioxyphenylacetate are refluxed for 6 hours in 0.3 ml of a 0.5M ethanolic potassium tert-butoxide solution. After dichloromethane and saturated aqueous sodium hydrogen carbonate solution have been added, the phases are separated. Purification by chromatography gives 2 mg (11%) of a solid, Rf=0.76 (dichloromethane/methanol=15:1).

Workup

  1. customthe phases are separated
  2. customPurification by chromatography

Sources & evidence

ORD record
ord-ea9c8567653745f3aba719a745352f3d
Source dataset
uspto-grants-2001_01
Patent number
US06174884B1

Reaction notes

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