反应详情

2,2,3,3-Tetrafluoropropylisothiocyanate (0.9 g.) and 2-(3-phthalimidopropylthio)-4-aminopyrimidine (0.9 g.) were dissolved in acetonitrile (30 ml.) and heated under reflux for 64 hours. The resulting suspension was cooled, filtered and the collected solid washed with acetonitrile (10 ml.) to give a white solid (0.9 g.). This was dissolved in a mixture of dimethylformamide (10 ml.) and saturated ethanolic ammonia solution (5 ml.) and treated with yellow mercuric oxide (0.8 g.). The mixture was stirred at room temperature for 3 hours. The solvent was evaporated and the black residue was triturated with ethyl acetate and filtered. The solvent was evaporated and the residual gum was dissolved in ethanol (15 ml.) and added to a solution of hydrazine (5 ml.) in ethanol (10 ml.). The mixture was stirred at room temperature for 2 hours then the solvent was evaporated. The residue was triturated with 1N hydrochloric acid, filtered and the filtrate was basified with 10N sodium hydroxide solution. The product was extracted with ethyl acetate, dried (magnesium sulphate) and the solvent was evaporated to give 4-[2-(2,2,3,3-tetrafluoropropyl)guanidino]-2-[3-aminopropylthio]pyrimidine (0.5 g.) which was used without further purification.

1. temperatureheated
2. temperatureunder reflux for 64 hours
3. temperatureThe resulting suspension was cooled
4. filtrationfiltered
5. washthe collected solid washed with acetonitrile (10 ml.)
6. customto give a white solid (0.9 g.)
7. customThe solvent was evaporated
8. customthe black residue was triturated with ethyl acetate
9. filtrationfiltered
10. customThe solvent was evaporated
11. dissolutionthe residual gum was dissolved in ethanol (15 ml.)
12. additionadded to a solution of hydrazine (5 ml.) in ethanol (10 ml.)
13. stirringThe mixture was stirred at room temperature for 2 hours
14. customthe solvent was evaporated
15. customThe residue was triturated with 1N hydrochloric acid
16. filtrationfiltered
17. extractionThe product was extracted with ethyl acetate
18. dry with materialdried (magnesium sulphate)
19. customthe solvent was evaporated