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

HRID 1664483

反応式

HRID 1664483 の反応式
[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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

Under argon, 75 mg (0.39 mmol) of 5-amino-1-cyclopentyl-1H-pyrazole-4-carbox-amide 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.

後処理

  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

出典と根拠

ORDレコード
ord-c3fc4ad2fdd040049ef1556a479e5504
出典データセット
uspto-grants-2011_10
特許番号
US08039477B2

関連ノート

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