Cesium carbonate → 2-(3-(5-(4-(Difluoromethoxy)phenyl)pyrimidin-2-ylamino)phenoxy)ethanol

HRID 2067899노트

반응식

HRID 2067899 반응식
[F:1][CH:2]([F:24])[O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:11]=[N:12][C:13]([NH:16][C:17]3[CH:18]=[C:19]([OH:23])[CH:20]=[CH:21][CH:22]=3)=[N:14][CH:15]=2)=[CH:6][CH:5]=1.Br[CH2:26][CH2:27][OH:28].C(=O)([O-])[O-].[Cs+].[Cs+]>C(#N)C>[F:24][CH:2]([F:1])[O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:15]=[N:14][C:13]([NH:16][C:17]3[CH:18]=[C:19]([CH:20]=[CH:21][CH:22]=3)[O:23][CH2:26][CH2:27][OH:28])=[N:12][CH:11]=2)=[CH:6][CH:5]=1

참가 물질

5

반응물 3

HCID 10796Cesium carbonateHCID 108982-BromoethanolHCID 687295593-(5-(4-(Difluoromethoxy)phenyl)pyrimidin-2-ylamino)phenol

생성물 1

HCID 687282992-(3-(5-(4-(Difluoromethoxy)phenyl)pyrimidin-2-ylamino)phenoxy)ethanol

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

A solution of 3-(5-(4-(difluoromethoxy)phenyl)pyrimidin-2-ylamino)phenol 39 (1.2 mmol), 2-bromoethanol (1.4 mmol) and cesium carbonate (1.6 mmol) in acetonitrile (10 mL) is heated to 85° C. for 12 h then cooled to rt. The reaction is evaporated to dryness then re-dissolved in DCM. The organic mixture is washed with water and brine then dried over magnesium sulfate, filtered and reduced to dryness. Purification by silica gel chromatography with hexane:EtOAc=1:1 as eluant affords 2-(3-(5-(4-(difluoromethoxy)phenyl)pyrimidin-2-ylamino)phenoxy)ethanol 40a as white solid. MS (m/z) (M+1)+: 373.8.

후처리

  1. customThe reaction is evaporated to dryness
  2. dissolutionthen re-dissolved in DCM
  3. washThe organic mixture is washed with water and brine
  4. dry with materialthen dried over magnesium sulfate
  5. filtrationfiltered
  6. customPurification by silica gel chromatography with hexane

출처 및 근거

ORD 기록
ord-77cc3b521a5e4bbdb994ecb109001f92
출처 데이터셋
uspto-grants-2012_10
특허 번호
US08293757B2

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