1,3,3,3-Tetrafluoro-1-methoxy-2-(trifluoromethyl)-1-propene → 4-Fluoro-6-methoxy-5-(trifluoromethyl)pyrimidine

HRID 1910876

Reaktionsgleichung

Reaktionsgleichung von HRID 1910876
[F:1][C:2](F)(F)[C:3]([C:8]([F:11])([F:10])[F:9])=[C:4](F)[O:5][CH3:6].C(O)(=O)C.[CH:18]([NH2:20])=[NH:19].[OH-].[Na+]>O.ClCCl>[F:1][C:2]1[C:3]([C:8]([F:11])([F:10])[F:9])=[C:4]([O:5][CH3:6])[N:20]=[CH:18][N:19]=1

Komponenten

6

Edukt 3

HCID 96721,3,3,3-Tetrafluoro-1-methoxy-2-(trifluoromethyl)-1-propeneHCID 14798Sodium HydroxideHCID 160693Formamidine acetate

Produkt 1

HCID 584392514-Fluoro-6-methoxy-5-(trifluoromethyl)pyrimidine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittel2×HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a rapidly stirred mixture of 1,1,1,3-tetrafluoro-2-(trifluoromethyl)-4-oxapent-2-ene (N-1) (10.0 g, 47.15 mmol) and formamidine acetate (7.37 g, 70.73 mmol) in a mixture of water (50 mL) and dichloromethane (50 mL) at 0° C., a solution of sodium hydroxide (7.54 g, 189 mmol) in water (40 mL) is added dropwise and the resulting mixture is stirred for 30 min after complete addition. The dichloromethane layer is separated, washed with 1M aqueous HCl solution and water, dried over Na2SO4 and filtered. The filtrate is concentrated in vacuo to afford 4-fluoro-6-methoxy-5-(trifluoromethyl)pyrimidine (N-2) as a yellow solid. The product is used directly in the next step without further purification.

Aufarbeitung

  1. additionafter complete addition
  2. customThe dichloromethane layer is separated
  3. washwashed with 1M aqueous HCl solution and water
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationThe filtrate is concentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-4df9d1f9ff3045cfaa39b8226f2bb6b6
Quelldatensatz
uspto-grants-2013_12
Patentnummer
US08604032B2

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