ORIGINAL ARTICLE
Year : 2013  |  Volume : 12  |  Issue : 2  |  Page : 186-192

Synthesis of new sulfanyl pyrimidin-4(3H)-one and ethyl-2-(pyridin-4yl) methoxy-1,2-dihydro-6-methyl-pyrimidine derivatives under conventional and heterogeneous conditions


1 Chemistry of Natural and Microbial Products Department and Pharmaceutical Research Group, Center of Excellence for Advanced Sciences, National Research Centre, Cairo, Egypt
2 Department of Medicinal Chemistry, National Research Centre, Cairo, Egypt

Correspondence Address:
Fatma A Bassyouni
Chemistry of Natural and Microbial Products Department and Pharmaceutical Research Group, Center of Excellence for Advanced Sciences, National Research Centre, 12311 Cairo
Egypt
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Source of Support: None, Conflict of Interest: None


DOI: 10.4103/1687-4315.124047

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Background and objectives Heterocyclic systems with a pyrimidine nucleus display a wide spectrum of biological activities, such as antimicrobial, antiviral, anticancer, antidepressive, anti-inflammatory, antitubercular, diuretic, and anticoagulant. The aim of the present study was the synthesis of new heterocyclic sulfanylpyrimidin-4(3H)-one derivatives by adopting simple and efficient methods, in addition to ethyl-2-(pyridin-4-yl) methoxy-1,2-dihydro-6-methyl-pyrimidine derivatives in excellent yields. Materials and methods The synthesis of the titled sulfanyl pyrimidin-4(3H)-one derivatives was achieved by the reaction of compounds 1a-c with phenacyl bromide, 4-methyl phenacyl bromide, or 4-nitrophenacyl bromide to give 5-(morpholin-4-ylmethyl)-2-oxoethylphenyl-sulfanyl-pyrimidin-4(3H)-ones (2a-c), [(4-methylpiperazin-1-yl) methyl]-2-oxoethylphenyl-sulfanyl-pyrimidin-4(3H)-ones (3a-c), or piperidin-1-yl) methyl]sulfanyl-pyrimidin-4(3H)-ones (4a-c), respectively. In addition, several heterocyclic pyrimidine derivatives such as ethyl-2-((pyridin-4-yl)methoxy-1,2-dihydro-6-methyl-pyrimidine derivatives 6a-h were prepared by the reaction of 1,2 dihydropyrimidone derivatives 5a-h with picolyl chloride using conventional and heterogeneous catalysts such as silica sulfuric acid and CuY-Zeolite. The structures of the synthesized compounds were confirmed by elemental analyses and spectroscopic methods. Results and conclusion A simple and efficient method was used for the synthesis of sulfanyl pyrimidin-4(3H)-one derivatives through reaction with different reagents. Also, ethyl-2-((pyridin-4-yl)methoxy-1,2-dihydro-6-methyl-pyrimidine derivatives were obtained using conventional and heterogeneous conditions in excellent yields.


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