Quinoline → 4-Chloro-6-(trifluoromethyl)pyrimidine

HRID 270585

Reaktionsgleichung

Reaktionsgleichung von HRID 270585
[F:1][C:2]([F:11])([F:10])[C:3]1[N:8]=[CH:7][N:6]=[C:5](O)[CH:4]=1.P(Cl)(Cl)([Cl:14])=O.N1C2C(=CC=CC=2)C=CC=1>C1(C)C=CC=CC=1.O>[Cl:14][C:5]1[CH:4]=[C:3]([C:2]([F:11])([F:10])[F:1])[N:8]=[CH:7][N:6]=1

Komponenten

6

Edukt 3

HCID 7047QuinolineHCID 24813Phosphorus oxychlorideHCID 178516143HCID 178516143, Verbindung

Produkt 1

HCID 115428814-Chloro-6-(trifluoromethyl)pyrimidineAusbeute 21,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittel

Versuchsvorschrift

A solution of 6-(trifluoromethyl)pyrimidin-4-ol (5.0 g, 30.5 mmol), phosphoryl chloride (3.41 mL, 36.6 mmol), and quinoline (2.16 mL, 18.3 mmol) in toluene (50 mL) was stirred at 100° C. for 5 h. The reaction was diluted with water and extracted with ethyl acetate three times, dried with sodium sulfate, filtered, and concentrated in vacuo. The crude residue was purified by flash column chromatography (10% EtOAc/Hexane) to yield the desired product (1.20 g, 21.6%). 1H NMR (400 MHz, CDCl3): 9.21 ppm (1H, s), 7.78 (1H, s).

Aufarbeitung

  1. extractionextracted with ethyl acetate three times
  2. dry with materialdried with sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe crude residue was purified by flash column chromatography (10% EtOAc/Hexane)

Quellen und Nachweise

ORD-Eintrag
ord-3e5f1f6159c54f4cab0d37db18e59b29
Quelldatensatz
uspto-grants-2008_11
Patentnummer
US07449467B2

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