5-alkoxy-1,2,4-triazolo[4,3-c]pyrimidine-3(2h)-thione...

Details 5-alkoxy-1,2,4-triazolo[4,3-c]pyrimidine-3(2h)-thione... 5-alkoxy-1,2,4-triazolo[4,3-c]pyrimidine-3(2h)-thione...

C - Chemistry, Metallurgy

07

D

C07D 487/04 (2006.01) A01N 43/90 (2006.01)

Patent

CA 2153246

5-Alkoxy(1,2,4)triazolo(1,5-c)pyrimidine-2(3H)-thione compounds (I), such as 5- ethoxy-8-fluoro(1,2,4)triazolo(1,5-c)pyrimidine-2(3H)-thione, were prepared by treatment of a 5-alkoxy-1,2,4-triazolo(4,3-c)-pyrimidine-3(2H)-thione compound (II), such as 5-ethoxy-8-fluoro-1,2,4-triazolo-(4,3-c)pyrimidine-3(2H)-thione, with an alkali metal alkoxide in an alcohol solvent slected so that the 5- alkoxy group, the alkoxide, and the alcohol all have the same alkyl group. The trialkylammonium salts of the 5-alkoxy-1,2,4-triazolo(4,3-c)-pyrimidine-3(2H)- thione compounds were converted to 3-hydrocarbylthio-5-alkoxy-1,2-4- triazolo(4,3-c)pyrimidine compounds by reaction with a hydrocarbyl halide, such as benzyl chloride. The products are useful intermediates in the preparation of 5-alkoxy(1,2,4)triazolo(1,5-c)pyrimidine-2-sulfonamide herbicides.

Cette invention se rapporte à des composés 5-alcoxy(1,2,4)triazolo(1,5-c)pyrimidine-2(3H)-thione (I), tels que 5-éthoxy-8-fluoro(1,2,4)triazolo(1,5-c)pyrimidine-2(3H)-thione, qu'on a préparés en traitant un composé 5-alcoxy-1,2,4-triazolo(4,3-c)-pyrimidine-3(2H)-thione (II) tel que 5-éthoxy-8-fluoro-1,2,4-triazolo-(4,3-c)pyrimidine-3(2H)-thione, avec un alcoxyde de métal alcalin dans un solvant à base d'alcool choisi pour que le groupe 5-alcoxy, l'alcoxyde et l'alcool aient tous le même groupe alkyle. Les sels trialkylammonium des composés 5-alcoxy-1,2,4-triazolo(4,3-c)-pyrimidine-3(2H)-thione ont été convertis en composés 3-hydrocarbylthio-5-alcoxy-1,2,4-triazolo(4,3c)pyrimidine, par réaction avec un halogénure hydrocarbyle, tel que du chlorure du benzyle. Ces produits sont utiles comme intermédiaires dans la préparation d'herbicides à base de 5-alcoxy(1,2,4)triazolo(1,5-c)pyrimidine-2-sulfonamide.

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