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   Synthesis of 2,3-dihydro-6-methyl-2-thiopyrimidin-4(1 H)-one (6-methylthiouracil) derivatives and their reactions  
   
نویسنده barmaki m. ,valiyeva g. ,maharramovm a.a. ,allaverdiyev m.m.
منبع journal of chemistry - 2013 - دوره : 2013 - شماره : 0
چکیده    The synthesis and characterization of 2,3-dihydro-6-methyl-2- thioxopyrimidin-(1h)-one (i) and some of its derivatives has been performed in our lab. ring-closing cyclization,as a result of the condensation of ethyl-3-oxobutanoate with thiourea in koh in an ethanol medium produced 2,3-dihydro-6-methy -2-thioxopyrimidin-(1h)-one (i). the reaction of compound (i) with 2- chloroacetic acid in an alkaline koh solution produced the carboxylate derivative,2-(2,6-dihydro-4-methyl-6-oxopyrimidin-2-yl-thio) ethanoic acid (ii). the reaction of the resulted derivative of carboxylate (ii) with the salt of copper sulphate,produced a new copper salt (iii). a substitution reaction between synthesized compound (i) and 2-chloroethanol in an aqueous solution of koh,created 2-(2-hydroxyethylthio)-6-methylpyrimidin-4(3h) -one (iv). the reaction of compound (i) with 2-(chloromethyl)oxirane in the presence of an aqueous solution of koh,resulted yielded 2-(3-chloro-2-hydroxy- propylthio)-6-methylpyrimidin-4(3h)-one (v). sodium mercaptide compound (vi),was produced by the reaction of (i) with naoh and then the sodium salt of 2,3-dihydro-6-methyl-2-thioxopyrimidin-(1h)-one (vi) was reacted with 2-(chloromethyl)oxirane to result in 2-((oxiran-2-yl) methyl-thio)-6-methyl- pyrimidin-4(3h)-one (vii). different acylation reagents (acetyl chloride,benzoyl chloride) were reacted with compound (i),in dimethylformamide,acylation happens on sulfur and furnished s-acylified derivatives of (viii-ix). all the synthesized and obtained products were confirmed by ir,1h,and 13c nmr and elemental analysis. © 2013 mohammad barmaki et al.
آدرس faculty of chemistry,north tehran branch,islamic azad university, ایران, department of chemistry,baku state university, Azerbaijan, department of chemistry,baku state university, Azerbaijan, department of chemistry,baku state university, Azerbaijan
 
     
   
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