Sodium Hydroxide → HCID 117821419, Verbindung

HRID 59088

Reaktionsgleichung

Reaktionsgleichung von HRID 59088
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][C:20]([F:25])([F:24])[CH2:21][CH2:22]O.[OH-].[Na+]>C1C=CC=CC=1.S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC>[Cl:18][C:9]1[N:10]=[C:11]([C:13]([O:15][CH2:16][CH3:17])=[CH2:14])[CH:12]=[C:7]([CH2:6][O:5][CH2:22][CH2:21][C:20]([F:25])([F:24])[F:19])[N:8]=1

Komponenten

6

Edukt 3

HCID 14798Sodium HydroxideHCID 1375123,3,3-Trifluoro-1-propanolHCID 117821115(2-Chloro-6-(1-ethoxyvinyl)pyrimidin-4-yl)methyl methanesulfonate

Produkt 1

HCID 117821419HCID 117821419, VerbindungAusbeute 11,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 94433Tetrabutylammonium hydrogen sulfateKatalysatorHCID 241BenzeneLösungsmittel

Versuchsvorschrift

To a solution of (2-chloro-6-(1-ethoxyvinyl)pyrimidin-4-yl)methyl methanesulfonate (0.452 g, 1.54 mmol) in benzene (7 mL) were added 3,3,3-trifluoropropan-1-ol (0.264 g, 2.32 mmol), sodium hydroxide (5 M, 0.463 mL, 2.32 mmol) and tetrabutylammonium hydrogen sulfate (0.052 g, 0.15 mmol). The mixture was stirred vigourously over night at room temperature. The mixture was filtered through a short silica plug with magnesium sulfate on top. The filter was washed with EtOAc. The mixture was purified by preparative HPLC to give 2-chloro-4-(1-ethoxyvinyl)-6-((3,3,3-trifluoropropoxy)methyl)pyrimidine 0.055 g 11%).

Aufarbeitung

  1. filtrationThe mixture was filtered through a short silica plug with magnesium sulfate on top
  2. washThe filter was washed with EtOAc
  3. customThe mixture was purified by preparative HPLC

Quellen und Nachweise

ORD-Eintrag
ord-858020decce040b0a2758796bc369d3b
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09439904B2

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