Synthesis and transformations of 1,3-bis[ω-(2-formylphenoxy)alkyl]-6-methyluracils

Reactions of salicylaldehyde sodium salt with 1,3-bis(omega-bromoalkyl)-6-methyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidines yielded 1,3-bis[omega-(2-formylphenoxy)alkyl]-6-methyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidines with the number of methylene units in the alkyl chains from 3 to 6. These products react with thiosemicarbazide to give the corresponding 1,3-bis[omega-(2-thiosemicarbazonophenoxy)alkyl]-6-methyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidine. Reduction with sodium borohydride of the aldehydes obtained in the first stage yields I,3-bis[omega-(2-hydroxymethylphenoxy)alkyl]-6-methyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidines, which react with thionyl chloride to give 1.,3-bis [omega-(2-chloromethylphenoxy)alkyl]-6-methyl-2,4-dioxo-1,2, 3,4-tetrahydropyrimidines. The latter products react wi th thiourea to give 1,3-bis [omega-(2-isothiuroniomethylphenoxy)alkyl] -6-methyl-2,4-dioxo-1,2,3 4-tetrahydropyrimidine chlorides whose hydrolysis in the presence of potassium carbonate yields 1,3-bis[omega-(2-mercaptomethylphenoxy)alkyl] 1,2,3,4-tetrahydropyrimidines.