反応 #46388

反応方程式

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

収率 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

収率 0.3%

溶媒

dimethylformamide

反応条件

後処理

1. 1
   温度the resulting mixture heated
2. 2
   温度at reflux under Dean-Stark conditions for 3 h
3. 3
   温度before refluxing for a further 20 h
4. 4
   温度The reaction mixture was cooled
5. 5
   ろ過filtered through kieselguhr
6. 6
   抽出The aqueous layer from the filtrate was extracted with ether
7. 7
   洗浄the combined ether extracts washed with water
8. 8
   その他dried
9. 9
   その他evaporated
10. 10
    抽出The aqueous was re-extracted with dichloromethane
11. 11
    その他the extract evaporated
12. 12
    その他The combined extracts were chromatographed on silica gel
13. 13
    洗浄eluting with methanol-dichloromethane mixtures

実験手順

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.

出典