Reacción #46388

Ecuación de reacción

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

→

title product

Rendimiento 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

Rendimiento 0.3%

Disolventes

dimethylformamide

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturathe resulting mixture heated
2. 2
   Temperaturaat reflux under Dean-Stark conditions for 3 h
3. 3
   Temperaturabefore refluxing for a further 20 h
4. 4
   TemperaturaThe reaction mixture was cooled
5. 5
   Filtraciónfiltered through kieselguhr
6. 6
   ExtracciónThe aqueous layer from the filtrate was extracted with ether
7. 7
   Lavadothe combined ether extracts washed with water
8. 8
   Otrodried
9. 9
   Otroevaporated
10. 10
    ExtracciónThe aqueous was re-extracted with dichloromethane
11. 11
    Otrothe extract evaporated
12. 12
    OtroThe combined extracts were chromatographed on silica gel
13. 13
    Lavadoeluting with methanol-dichloromethane mixtures

Procedimiento

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.

Fuente