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

HRID 59084

Reaktionsgleichung

Reaktionsgleichung von HRID 59084
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

Komponenten

6

Edukt 3

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 94433Tetrabutylammonium hydrogen sulfateKatalysatorHCID 241BenzeneLösungsmittel

Versuchsvorschrift

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%).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-4c6906f8869b4deab1d78f128dc10bbd
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09439904B2

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