Réaction #46388

Équation de réaction

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

Rendement 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

Rendement 0.3%

Solvants

dimethylformamide

Conditions de réaction

Traitement

1. 1
   Températurethe resulting mixture heated
2. 2
   Températureat reflux under Dean-Stark conditions for 3 h
3. 3
   Températurebefore refluxing for a further 20 h
4. 4
   TempératureThe reaction mixture was cooled
5. 5
   Filtrationfiltered through kieselguhr
6. 6
   ExtractionThe aqueous layer from the filtrate was extracted with ether
7. 7
   Lavagethe combined ether extracts washed with water
8. 8
   Autredried
9. 9
   Autreevaporated
10. 10
    ExtractionThe aqueous was re-extracted with dichloromethane
11. 11
    Autrethe extract evaporated
12. 12
    AutreThe combined extracts were chromatographed on silica gel
13. 13
    Lavageeluting with methanol-dichloromethane mixtures

Mode opératoire

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.

Source