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 Buchi Sincore 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.

Radi, M., Petricci, E., Maga, G., Corelli, F., Botta, M. (2005). Parallel solution phase synthesis of 4-dialkylamino-2-methylsulfonyl-6-vinylpyrimidines. JOURNAL OF COMBINATORIAL CHEMISTRY, 7(1), 117-122 [10.1021/cc049880u].

Parallel solution phase synthesis of 4-dialkylamino-2-methylsulfonyl-6-vinylpyrimidines

Petricci, E.;Maga, G.;Corelli, F.;Botta, M.
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 Buchi Sincore 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
Radi, M., Petricci, E., Maga, G., Corelli, F., Botta, M. (2005). Parallel solution phase synthesis of 4-dialkylamino-2-methylsulfonyl-6-vinylpyrimidines. JOURNAL OF COMBINATORIAL CHEMISTRY, 7(1), 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/11365/19053