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 / Radi, Marco; Elena, Petricci; Giovanni, Maga; Federico, Corelli; Maurizio, Botta. - In: JOURNAL OF COMBINATORIAL CHEMISTRY. - ISSN 1520-4766. - 7:(2005), pp. 117-122. [10.1021/cc049880u]

Parallel Solution-Phase Synthesis of 4-Dialkylamino-2-methylsulfonyl-6-vinylpyrimidines

RADI, Marco;
2005-01-01

Abstract

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.
2005
Parallel Solution-Phase Synthesis of 4-Dialkylamino-2-methylsulfonyl-6-vinylpyrimidines / Radi, Marco; Elena, Petricci; Giovanni, Maga; Federico, Corelli; Maurizio, Botta. - In: JOURNAL OF COMBINATORIAL CHEMISTRY. - ISSN 1520-4766. - 7:(2005), pp. 117-122. [10.1021/cc049880u]
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11381/2432283
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