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

HRID 566345Notes

Reaction equation

HRID 566345 reaction equation
[NH2:1][C:2]1[N:6]([CH:7]([CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])[CH3:8])[N:5]=[C:4]([CH3:15])[C:3]=1[C:16]([NH2:18])=[O:17].[CH2:19]1[O:27][C:26]2[CH:25]=[CH:24][C:23]([CH2:28][C:29](OC)=O)=[CH:22][C:21]=2[O:20]1.CC(C)([O-])C.[K+].C(=O)([O-])O.[Na+]>ClCCl>[CH2:19]1[O:27][C:26]2[CH:25]=[CH:24][C:23]([CH2:28][C:29]3[NH:18][C:16](=[O:17])[C:3]4[C:4]([CH3:15])=[N:5][N:6]([CH:7]([CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])[CH3:8])[C:2]=4[N:1]=3)=[CH:22][C:21]=2[O:20]1

Participants

6

Reactant 4

HCID 266588Methyl 2-(1,3-dioxaindan-5-yl)acetateHCID 516892Sodium BicarbonateHCID 23665647Potassium tert-butoxideHCID 599323335-amino-3-methyl-1-(2-octyl)-1H-pyrazole-4-carboxamide

Product 1

HCID 1361321416-(3,4-Methylenedioxy-benzyl)-1-(2-octyl)-3-methyl-1,5-dihydro-pyrazolo[3,4-d]pyrimidin-4-oneYield 16%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

10 mg (0.037 mmol) of 5-amino-3-methyl-1-(2-octyl)-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 (16%) of a solid, Rf=0.67 (dichloromethane/methanol=15:1).

Workup

  1. customthe phases are separated
  2. customPurification by chromatography

Sources & evidence

ORD record
ord-c831c4d9e41c4f099319a601e91fa3e8
Source dataset
uspto-grants-2001_01
Patent number
US06174884B1

Reaction notes

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