Sodium Hydroxide → 2-Chloro-4-((1,3-difluoropropan-2-yloxy)methyl)-6-(1-ethoxyvinyl)pyrimidine

HRID 59084

반응식

HRID 59084 반응식
CS([O:5][CH2:6][C:7]1[CH:12]=[C:11]([C:13]([O:15][CH2:16][CH3:17])=[CH2:14])[N:10]=[C:9]([Cl:18])[N:8]=1)(=O)=O.[F:19][CH2:20][CH:21](O)[CH2:22][F:23].[OH-].[Na+]>C1C=CC=CC=1.S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC>[Cl:18][C:9]1[N:8]=[C:7]([CH2:6][O:5][CH:21]([CH2:22][F:23])[CH2:20][F:19])[CH:12]=[C:11]([C:13]([O:15][CH2:16][CH3:17])=[CH2:14])[N:10]=1

참가 물질

6

반응물 3

HCID 14798Sodium HydroxideHCID 679851,3-Difluoro-2-propanolHCID 117821115(2-Chloro-6-(1-ethoxyvinyl)pyrimidin-4-yl)methyl methanesulfonate

생성물 1

HCID 1213172292-Chloro-4-((1,3-difluoropropan-2-yloxy)methyl)-6-(1-ethoxyvinyl)pyrimidine수율 11%

시약·촉매·용매 2

HCID 94433Tetrabutylammonium hydrogen sulfate촉매HCID 241Benzene용매

실험 절차

To a solution of (2-chloro-6-(1-ethoxyvinyl)pyrimidin-4-yl)methyl methanesulfonate (0.50 g, 1.71 mmol) in benzene (10 mL), was added 1,3-difluoro-2-propanol (0.246 g, 2.56 mmol). Sodium hydroxide (5M (aq), 0.512 mL, 2.56 mmol) and tetrabutylammonium hydrogen sulfate (0.058 g, 0.17 mmol) were added. The mixture was stirred vigorously at rt over night. The mixture was filtered through a short silica plug with magnesium sulfate. The filter plug was eluted with EtOAc and the solvents were evaporated. The residue was purified by preparative HPLC to give the title compound as a solid (0.054 g, 11%).

후처리

  1. filtrationThe mixture was filtered through a short silica plug with magnesium sulfate
  2. washThe filter plug was eluted with EtOAc
  3. customthe solvents were evaporated
  4. customThe residue was purified by preparative HPLC

출처 및 근거

ORD 기록
ord-4c6906f8869b4deab1d78f128dc10bbd
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09439904B2

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