Microwave-assisted solution- and solid-phase synthesis of 2-amino-4-arylpyrimidine derivatives.
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.
Matloobi
Mitra
M
Christian Doppler Laboratory for Microwave Chemistry (CDLMC) and Institute of Chemistry, Karl-Franzens-University, Heinrichstrasse 28, A-8010 Graz, Austria.
Kappe
C Oliver
CO
D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D008872:Microwaves; D011743:Pyrimidines / Q000138:chemical synthesis* / Q000737:chemistry
D011743:Pyrimidines