Water → 4-[2-(3-Chloro-2-methyl-phenoxy)-pyrimidin-4-yloxy]-2,5-dimethyl-phenylamine

HRID 12085

反応式

HRID 12085 の反応式
[Cl:1][C:2]1[C:3]([CH3:9])=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.[H-].[Na+].Cl[C:13]1[N:18]=[C:17]([O:19][C:20]2[C:25]([CH3:26])=[CH:24][C:23]([NH2:27])=[C:22]([CH3:28])[CH:21]=2)[CH:16]=[CH:15][N:14]=1.O>C1COCC1>[Cl:1][C:2]1[C:3]([CH3:9])=[C:4]([CH:5]=[CH:6][CH:7]=1)[O:8][C:13]1[N:18]=[C:17]([O:19][C:20]2[C:25]([CH3:26])=[CH:24][C:23]([NH2:27])=[C:22]([CH3:28])[CH:21]=2)[CH:16]=[CH:15][N:14]=1

参加物

6

反応物 4

HCID 962WaterHCID 148563-Chloro-o-cresolHCID 24758Sodium hydrideHCID 866289744-(2-Chloro-pyrimidin-4-yloxy)-2,5-dimethyl-phenylamine

生成物 1

HCID 670264424-[2-(3-Chloro-2-methyl-phenoxy)-pyrimidin-4-yloxy]-2,5-dimethyl-phenylamine

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
60 °C

実験手順

A solution of 1.43 g (10 mmol) 3-chloro-2-methyl-phenol and 0.4 g sodium hydride (60% in paraffine, 10 mmol) in 20 ml THF were stirred for 30 min at ambient temperature. After adding 1.25 g (5 mmol) 4-(2-chloro-pyrimidin-4-yloxy)-2,5-dimethyl-phenylamine the mixture was stirred for 20 hrs at 60° C. After cooling down to ambient temperature 20 ml water was added and the organic layer was separated, dried over magnesium sulfate, concentrated in vacuo, column chromatography (cycclhexane/ethyl acetate, 2:1) and a second column chromatography (dichloromethane) yielded 640 mg (30%) with a purity of 85%; log P (pH=2.3)=2.81.

後処理

  1. additionwas added
  2. customthe organic layer was separated
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated in vacuo, column chromatography (cycclhexane/ethyl acetate, 2:1)
  5. customa second column chromatography (dichloromethane) yielded 640 mg (30%) with a purity of 85%

出典と根拠

ORDレコード
ord-83ad101b069c418abead533afb70f9d8
出典データセット
uspto-grants-2010_06
特許番号
US07727986B2

関連ノート

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