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

HRID 566343Notes

Reaction equation

HRID 566343 reaction equation
[NH2:1][C:2]1[N:6]([CH:7]([CH:17]([OH:19])[CH3:18])[CH2:8][CH2:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[N:5]=[CH:4][C:3]=1[C:20]([NH2:22])=[O:21].[CH2:23]1[O:31][C:30]2[CH:29]=[CH:28][C:27]([CH2:32][C:33](OC)=O)=[CH:26][C:25]=2[O:24]1.CC(C)([O-])C.[K+].C(=O)([O-])O.[Na+]>ClCCl>[CH2:23]1[O:31][C:30]2[CH:29]=[CH:28][C:27]([CH2:32][C:33]3[NH:22][C:20](=[O:21])[C:3]4[CH:4]=[N:5][N:6]([CH:7]([CH:17]([OH:19])[CH3:18])[CH2:8][CH2:9][CH2:10][C:11]5[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=5)[C:2]=4[N:1]=3)=[CH:26][C:25]=2[O:24]1

Participants

6

Reactant 4

HCID 266588Methyl 2-(1,3-dioxaindan-5-yl)acetateHCID 516892Sodium BicarbonateHCID 212660785-Amino-1-[1-(1-hydroxy-ethyl)-4-phenyl-butyl]-1H-pyrazole-4-carboxamideHCID 23665647Potassium tert-butoxide

Product 1

HCID 1357028616-(3,4-Methylenedioxy-benzyl)-1-[1-(1-hydroxy-ethyl)-4-phenyl-butyl]-1,5-dihydro-pyrazolo[3,4-d]pyrimidin-4-oneYield 64.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

20 mg (0.066 mmol) of 5-amino-1-[1-(1-hydroxy-ethyl)-4-phenyl-butyl]-1H-pyrazole-4-carboxamide and 41 mg (0.210 mmol) of methyl 3,4-methylenedioxyphenylacetate are refluxed for 6 hours in 1.06 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 19 mg (64%) of a solid, Rf=0.20 (dichloromethane/methanol=15:1).

Workup

  1. customthe phases are separated
  2. customPurification by chromatography

Sources & evidence

ORD record
ord-79b7d0735fd240b78d252beabf547a3f
Source dataset
uspto-grants-2001_01
Patent number
US06174884B1

Reaction notes

Loading…