A simple and straightforward methodology for the parallel, solution-phase synthesis of novel 4-dialkylamino-2-methylsulfonyl-6-vinylpyrimidines 9a-j has been developed. Starting from 2-methylthio-6-[2-(p-toluensulfonyloxy)ethan-1-yl] -4(3H)-pyrimidinone (6), a three-step procedure (namely, tosylate substitution by amines, base-catalyzed rearrangement, and sulfide to sulfone oxidation) using a Büchi Sincere synthesizer gave the final products in high yield after simple ethyl acetate extraction and without further purification. Interestingly, when the final oxidation step was performed on 4-arylpiperazine derivatives 8g-j, the corresponding highly polar piperazine N-oxides 9g-j were obtained, which conversely needed chromatographic purification in order to give the pure products.
Parallel Solution-Phase Synthesis of 4-Dialkylamino-2-methylsulfonyl-6-vinylpyrimidines / Marco Radi;Elena Petricci;Giovanni Maga;Federico Corelli;Maurizio Botta. - In: JOURNAL OF COMBINATORIAL CHEMISTRY. - ISSN 1520-4766. - 7(2005), pp. 117-122.