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2-(4-Methylcyclohexyl)acetic acid → 6-[(4-Methylcyclohexyl)methyl]-1-(2-methylphenyl)-1,5-dihydropyrazolo[3,4-d]pyrimidin-4-one

HRID 68935
ノート
印刷プレビュー

反応式

HRID 68935 の反応式
[NH2:1][C:2]1[N:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[CH3:13])[N:5]=[CH:4][C:3]=1[C:14]([NH2:16])=[O:15].[CH3:17][CH:18]1[CH2:23][CH2:22][CH:21]([CH2:24][C:25](O)=O)[CH2:20][CH2:19]1.C[Si](OP(=O)=O)(C)C>O>[CH3:17][CH:18]1[CH2:23][CH2:22][CH:21]([CH2:24][C:25]2[NH:16][C:14](=[O:15])[C:3]3[CH:4]=[N:5][N:6]([C:7]4[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=4[CH3:13])[C:2]=3[N:1]=2)[CH2:20][CH2:19]1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 36169452-(4-Methylcyclohexyl)acetic acidHCID 119839075-Amino-1-(o-tolyl)-1H-pyrazole-4-carboxamideHCID 16133246Trimethyl(phosphooxy)silane

生成物 1

HCID 1355084206-[(4-Methylcyclohexyl)methyl]-1-(2-methylphenyl)-1,5-dihydropyrazolo[3,4-d]pyrimidin-4-one

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
130 °C

実験手順

150 mg (0.69 mmol) of 5-amino-1-(2-methylphenyl)-1H-pyrazole-4-carboxamide (Example 23A) and 130 mg (0.83 mmol) of 2-(4-methylcyclohexyl)acetic acid are mixed with 0.3 ml of trimethylsilyl polyphosphate and stirred at 130° C. for 3 h. The hot reaction mixture is added to 20 ml of water and then extracted with dichloromethane (2×20 ml). The combined organic phases are washed with water (20 ml) and with saturated sodium chloride solution (20 ml) and dried over sodium sulphate. The solvent is distilled off under reduced pressure, and the crude product is purified by preparative HPLC (YMC Gel ODS-AQ S 5/15 μm; eluent. A: water, eluent B: acetonitrile; gradient: 0 min 30% B, 5 min 30% B, 50 min 95% B). 182 g (78% of theory) of the product are obtained.

後処理

  1. extractionextracted with dichloromethane (2×20 ml)
  2. washThe combined organic phases are washed with water (20 ml) and with saturated sodium chloride solution (20 ml)
  3. dry with materialdried over sodium sulphate
  4. distillationThe solvent is distilled off under reduced pressure
  5. customthe crude product is purified by preparative HPLC (YMC Gel ODS-AQ S 5/15 μm
  6. custom0 min 30% B, 5 min 30% B, 50 min 95% B
  7. custom182 g (78% of theory) of the product are obtained

出典と根拠

ORDレコード
ord-d4bbf5dfbc94414a99d88a05cef1d4c4
出典データセット
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08822479B2

反応ノート

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このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート