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

HRID 566347Notes

Reaction equation

HRID 566347 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].[CH2:20]1[O:28][C:27]2[CH:26]=[CH:25][C:24]([CH2:29][C:30](OC)=O)=[CH:23][C:22]=2[O:21]1.[O-]CC.[Na+].C(=O)([O-])O.[Na+]>ClCCl>[CH2:20]1[O:28][C:27]2[CH:26]=[CH:25][C:24]([CH2:29][C:30]3[NH:19][C:17](=[O:18])[C:3]4[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]=4[N:1]=3)=[CH:23][C:22]=2[O:21]1

Participants

6

Reactant 4

HCID 266588Methyl 2-(1,3-dioxaindan-5-yl)acetateHCID 516892Sodium BicarbonateHCID 2723922Sodium ethoxideHCID 599323475-amino-3-methyl-(3-nonyl)-1H-pyrazole-4-carboxamide

Product 1

HCID 1363863776-(3,4-Methylenedioxy-benzyl)-1-(3-nonyl)-3-methyl-1,5-dihydro-pyrazolo[3,4-d]pyrimidin-4-oneYield 52.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

15 mg (0.055 mmol) of 5-amino-3-methyl-1-(3-nonyl)-1H-pyrazole-4-carboxamide and 53 mg (0.274 mmol) of methyl 3,4-methylenedioxyphenylacetate 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 11.8 mg (52%) of a solid, Rf=0.65 (dichloromethane/methanol=15:1).

Workup

  1. customthe phases are separated
  2. customPurification by chromatography

Sources & evidence

ORD record
ord-927a85a5acbb40a18c17c0d9c3c7575a
Source dataset
uspto-grants-2001_01
Patent number
US06174884B1

Reaction notes

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