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

HRID 12085

반응식

HRID 12085 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
60 °C

실험 절차

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.

후처리

  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%

출처 및 근거

ORD 기록
ord-83ad101b069c418abead533afb70f9d8
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07727986B2

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