반응 #46388

반응 방정식

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

수율 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

수율 0.3%

용매

dimethylformamide

반응 조건

후처리

1. 1
   온도the resulting mixture heated
2. 2
   온도at reflux under Dean-Stark conditions for 3 h
3. 3
   온도before refluxing for a further 20 h
4. 4
   온도The reaction mixture was cooled
5. 5
   여과filtered through kieselguhr
6. 6
   추출The aqueous layer from the filtrate was extracted with ether
7. 7
   세척the combined ether extracts washed with water
8. 8
   기타dried
9. 9
   기타evaporated
10. 10
    추출The aqueous was re-extracted with dichloromethane
11. 11
    기타the extract evaporated
12. 12
    기타The combined extracts were chromatographed on silica gel
13. 13
    세척eluting with methanol-dichloromethane mixtures

실험 절차

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.

출처