Parallel solution-phase synthesis of 4-dialkylamino-2-methylsulfonyl-6-vinylpyrimidines.
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
Marco
M
Dipartimento di Farmaco Chimico Tecnologico, Università degli Studi di Siena, Via A. Moro, 53100-Siena, Italy.
Petricci
Elena
E
Maga
Giovanni
G
Corelli
Federico
F
Botta
Maurizio
M
D000478:Alkylation; D000588:Amines / Q000737:chemistry*; D020650:Combinatorial Chemistry Techniques; D008745:Methylation; D015394:Molecular Structure; D011743:Pyrimidines / Q000138:chemical synthesis* / Q000737:chemistry*; D012996:Solutions / Q000737:chemistry*; D013455:Sulfur / Q000737:chemistry*
D000588:Amines; D011743:Pyrimidines; D012996:Solutions; D013455:Sulfur