Novel Synthesis Approach and Antiplatelet Activity Evaluation of 6-Arylmethyleneamino-2-Alkylsulfonylpyrimidin-4(3H)-one Derivatives and Its Nucleosides

A new and efficient procedure has been designed for the preparation of 6-arylmethylene-amino-2-alkyl sulfonylpyrimidine. The first alkylthio group was introduced into the pyrimidine ring by S-alkylation. The introduction of the second one was successfully achieved using the phosphorous oxychloride method to afford 4-chloro-2-alkylthiopyrimidines. Subsequent nucleophilic displacement by the corresponding alkylamines followed by glycoside bromide addition conveniently gave a series of the target compounds. Thus, the two same or different alkylamino groups were easily introduced into the pyrimidine ring through the two different approaches. The human anti-platelet aggregation activity of the newly synthesized compounds was also described.