Reaktion #46388

Reaktionsgleichung

compound

1-{(S)-2-[(5-Bromo-pyrimidin-2-ylamino)-methyl]-pyrrolidin-1-yl}-1-[5-(4-fluoro-phenyl)-2-methyl-thiazol-4-yl]-methanone

potassium trifluoroacetate

toluene

water ether

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title product

Ausbeute 0.3%

1-[5-(4-Fluoro-phenyl)-2-methyl-thiazol-4-yl]-1-{(S)-2-[(5-trifluoromethyl-pyrimidin-2-ylamino)-methyl]-pyrrolidin-1-yl}-methanone

Ausbeute 0.3%

Lösungsmittel

dimethylformamide

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturthe resulting mixture heated
2. 2
   Temperaturat reflux under Dean-Stark conditions for 3 h
3. 3
   Temperaturbefore refluxing for a further 20 h
4. 4
   TemperaturThe reaction mixture was cooled
5. 5
   Filtrationfiltered through kieselguhr
6. 6
   ExtraktionThe aqueous layer from the filtrate was extracted with ether
7. 7
   Waschenthe combined ether extracts washed with water
8. 8
   Sonstigedried
9. 9
   Sonstigeevaporated
10. 10
    ExtraktionThe aqueous was re-extracted with dichloromethane
11. 11
    Sonstigethe extract evaporated
12. 12
    SonstigeThe combined extracts were chromatographed on silica gel
13. 13
    Wascheneluting with methanol-dichloromethane mixtures

Vorschrift

To the compound from Example 194 (0.36 g) in dimethylformamide (5 ml) was added potassium trifluoroacetate (0.23 g), copper iodide (0.3 g) and toluene (5 ml) and the resulting mixture heated at reflux under Dean-Stark conditions for 3 h, before refluxing for a further 20 h. The reaction mixture was cooled, poured into water/ether and filtered through kieselguhr. The aqueous layer from the filtrate was extracted with ether, and the combined ether extracts washed with water, dried and evaporated. The aqueous was re-extracted with dichloromethane and the extract evaporated. The combined extracts were chromatographed on silica gel, eluting with methanol-dichloromethane mixtures, to afford the title product (0.001 g). Mass Spectrum (Electrospray LC/MS): Found 466 (MH+). C21H19F4N5OS requires 465.

Quelle