Benzeneacetic acid, 3,4-dimethoxy-, methyl ester → 6-(3,4-Dimethoxy-benzyl)-1-[1-(1-hydroxy-ethyl)-4-phenyl-butyl]-3-ethyl-1,5-dihydro-pyrazolo[3,4-d]pyrimidin-4-one

HRID 566342

Reaction equation

HRID 566342 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]=[C:4]([CH2:20][CH3:21])[C:3]=1[C:22]([NH2:24])=[O:23].CC(C)([O-])C.[K+].[CH3:31][O:32][C:33]1[CH:34]=[C:35]([CH2:41][C:42](OC)=O)[CH:36]=[CH:37][C:38]=1[O:39][CH3:40].C1CCCCC1.C(OCC)(=O)C>C(O)C>[CH3:31][O:32][C:33]1[CH:34]=[C:35]([CH:36]=[CH:37][C:38]=1[O:39][CH3:40])[CH2:41][C:42]1[NH:24][C:22](=[O:23])[C:3]2[C:4]([CH2:20][CH3:21])=[N:5][N:6]([CH:7]([CH:17]([OH:19])[CH3:18])[CH2:8][CH2:9][CH2:10][C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:2]=2[N:1]=1

Participants

6

Reactant 4

HCID 85213Benzeneacetic acid, 3,4-dimethoxy-, methyl esterHCID 212660795-amino-1-[1-(1-hydroxy-ethyl)-4-phenyl-butyl]-3-ethyl-1H-pyrazole-4-carboxamideHCID 21867204Cyclohexane ethylacetate2×HCID 23665647Potassium tert-butoxide

Product 1

HCID 1357028686-(3,4-Dimethoxy-benzyl)-1-[1-(1-hydroxy-ethyl)-4-phenyl-butyl]-3-ethyl-1,5-dihydro-pyrazolo[3,4-d]pyrimidin-4-one

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1.0 g (3.03 mmol) of 5-amino-1-[1-(1-hydroxy-ethyl)-4-phenyl-butyl]-3-ethyl-1H-pyrazole-4-carboxamide, 1.60 g of potassium tert-butoxide and 1.40 g (19 mmol) of methyl 3,4-dimethoxyphenylacetate are refluxed overnight in 20 ml of ethanol. The solvent is removed in vacuo, the residue is taken up in dichloromethane, the mixture is extracted with 1N HCl, the organic phase is dried over Na2SO4 and evaporated on a rotary evaporator. Purification by chromatography (cyclohexane/EA=2:1, 1% formic acid) and separation of the diastereomers by chromatography gives 232 mg (16%) of the diastereomer which elutes more rapidly, Rf=0.2 (cyclohexane/ethyl acetate=2:1) and 150 mg (10%) of the diastereomer which elutes more slowly, Rf=0.15 (cyclohexane/ethyl acetate=2:1).

Workup

  1. customThe solvent is removed in vacuo
  2. extractionthe mixture is extracted with 1N HCl
  3. dry with materialthe organic phase is dried over Na2SO4
  4. customevaporated on a rotary evaporator
  5. customPurification
  6. customby chromatography (cyclohexane/EA=2:1, 1% formic acid) and separation of the diastereomers by chromatography
  7. customgives 232 mg (16%) of the diastereomer which

Sources & evidence

ORD record
ord-6a03ab62641d4043a3ee743ddf4826c8
Source dataset
uspto-grants-2001_01
Patent number
US06174884B1

Linked notes

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