Synthesis of Substituted Pyrimidin-4(1H)-one (Uracil) Derivatives and Some of Their Reactions

Abstract

In this paper I described two practical routes for the synthesis of substituted Uracilderivatives and achieved some of their reactions. In the first synthesis which is based on the condensation reaction of ethyl 2- cyanoacetate and thiourea, the cyclized compound 6-amino-2mercaptopyrimidin-4(3H)-one (I) achieved in the presence of sodium ethanoate. Thecompund (I) react with 2-(chloromethyl)oxirane in the given medium (II) was produced, then treated in medium of ethanol in peresence of KOH which new recyclized product 8-amino-3,4-dihydro-3hydroxypyrimido[2,1-b][1,3]thiazin-6(2H)-one (III) was obtained.The other ring closing cyclization proceeded 6-methyl-2,3-dihydro-2-thioxopyrimidin-4(1H)-one (IV) by ethyl acetoacetate and thiourea in ethyl alcohol and potassium hydroxide medium. In the next reaction, firstly Sodium Salt of (V) was gained, then it was reacted with 2-(chloromethyl)oxirane. At the end, substitued derivative (VI) was resulted.All synthesized products were confirmed by IR, ¹H NMR, ¹³C NMR, and elemental analysis. All the experimental data is described extensively in this report.