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

HRID 400491

Reaktionsgleichung

Reaktionsgleichung von HRID 400491
[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

Komponenten

6

Edukt 4

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

Under argon, 75 mg (039 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; L35 mmol, 15 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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-b4f99a1e32184dcc8b2f023c3b1bc9c8
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08741907B2

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