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Reactions of 5-(2-Dimethylamino-6-methyl-4-pyrimidinylsulfanylmethyl)-1,3,4-oxadiazole-2-thione with carbon Electrophiles

Burbuliene M., Udrenaite E., Gaidelis P., Vainilavicius P.

Polish Journal of Chemistry

2002

Vol. 76 / nr 4

557-563

From 2,4-dichloro-6-methylpyrimidine (1) via esters 2 and 3, (2-dimethylamino-6- methyl-4-pyrimidinylsulfanyl)acethydrazide (4) was synthesized. The latter under treatment either with carbon disulfide in the presence of a base or with potassium O-ethylxanthate in ethanol yielded 5-(2-dimethylamino-6-methyl-4-pyrimidinylsulfanylmethyl)-1,3,4- oxadiazole-2-thione (5). Alkylation of 5 afforded S-alkyl derivatives 6a,b, whereas aminomethylation, acylation or cyanoethylation gave N(3)-substituted derivatives 7-9. Compounds were tested for their anti-inflammatory activity.