Ethanol → 6-(Cyclohexylmethyl)-1-cyclopentyl-1,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one

HRID 16234

Reaction equation

HRID 16234 reaction equation
[NH2:1][C:2]1[N:6]([CH:7]2[CH2:11][CH2:10][CH2:9][CH2:8]2)[N:5]=[CH:4][C:3]=1[C:12]([NH2:14])=[O:13].[CH:15]1([CH2:21][C:22](OC)=O)[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1.C(O)C.[H-].[Na+]>O>[CH:15]1([CH2:21][C:22]2[NH:14][C:12](=[O:13])[C:3]3[CH:4]=[N:5][N:6]([CH:7]4[CH2:11][CH2:10][CH2:9][CH2:8]4)[C:2]=3[N:1]=2)[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1

Participants

6

Reactant 4

HCID 702EthanolHCID 24758Sodium hydrideHCID 139743Cyclohexaneacetic acid, methyl esterHCID 117011915-amino-1-cyclopentyl-1H-pyrazole-4-carboxamide

Product 1

HCID 1354071776-(Cyclohexylmethyl)-1-cyclopentyl-1,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Under argon, 75 mg (0.39 mmol) of 5-amino-1-cyclopentyl-1H-pyrazole-4-carboxamide and 183 mg (1.16 mmol, 3 equiv.) of methyl cyclohexylacetate are introduced into 1.5 ml of absolute ethanol. At 0° C., 54 mg of sodium hydride (60% dispersion in mineral oil; 1.35 mmol, 3.5 equiv.) are slowly added in a countercurrent of argon. The resulting mixture is slowly heated and stirred under reflux for 18 h. For workup, 20 ml of water are added, and the mixture is extracted several times with ethyl acetate. The combined organic phases are dried over sodium sulfate and concentrated in vacuo. The crude product is purified by preparative HPLC.

Workup

  1. temperatureThe resulting mixture is slowly heated
  2. temperatureunder reflux for 18 h
  3. extractionthe mixture is extracted several times with ethyl acetate
  4. dry with materialThe combined organic phases are dried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe crude product is purified by preparative HPLC

Sources & evidence

ORD record
ord-83942128d5134714a4574f3a05846204
Source dataset
uspto-grants-2010_06
Patent number
US07737156B2

Linked notes

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