Microwave-Assisted Solution- and Solid-Phase Synthesis of 2-Amino-4-arylpyrimid Derivatives

Mitra Matloobi and C. Oliver Kappe, Karl-Franzens-University Graz

Date Posted: Thursday, September 21, 2006

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Abstract
An efficient and rapid microwave-assisted solution-phase method for the synthesis of 2-amino-4-arylpyrimidine-5-carboxylic acid derivatives has been developed. The five step linear protocol involves an initial Biginelli multicomponent reaction leading to dihydropyrimidine-2-thiones which are subsequently S-alkylated with methyl iodide.

The resulting 2-methylthiodihydropyrimidines are sequentially oxidized first with manganese dioxide and then with Oxone to provide 2-methylsulfonyl-pyrimidines which serve as excellent precursors for the generation of a variety of 2-substituted pyrimidines via displacement of the reactive sulfonyl group with nitrogen, oxygen, sulfur and carbon nucleophiles. A modified protocol using a solid-phase method has also been developed

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