The chemistry of certain tetrahydropyrimidines Public Deposited

http://ir.library.oregonstate.edu/concern/graduate_thesis_or_dissertations/5h73pz74c

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  • Since many 1, 4, 5, 6-tetrahydropyrimidines have become available and commercially useful in recent years, a study of the chemistry of certain of these compounds has been undertaken. 2-Hydroxy- and 2-mercapto-1, 4, 5, 6-tetrahydropyrimidine have been synthesized by the condensation of urea and thiourea, respectively, with 1, 3-propanediamine, with yields of 30 and 50 percent. 2-Phenyl-1, 4, 5, 6-tetrahydropyrimidine hydrochloride was prepared in quantitative yield by the addition of hydrogen chloride gas to the free base in either benzene or absolute ethanol. A nuclear acylation of 2-phenyl-1, 4, 5, 6-tetrahydropyrimidine with acetic anhydride produced 1-acetyl-2-phenyl-1, 4, 5, 6-tetrahydropyrimidine in about 70 percent yield. The same reaction with 2-methyl-1, 4, 5, 6-tetrahydropyrimidine gave an unidentified amorphous material. 2-Phenyl-1, 4, 5, 6-tetrahydropyrimidine hydrolyzed in an aqueous solution to only a small extent at room temperature; however, at 100 degrees, the tetrahydropyrimidine ring was completely disrupted after one hour. Some destruction of the ring was also observed in boiling xylene and in boiling ethanol. 2-Amino-1, 4, 5, 6-tetrahydropyrimidine hydrolyzed slowly in neutral and alkaline media at room temperature; it was found to be less stable in an alkaline solution than in a neutral one. Dehydrogenation of 1, 4, 5, 6-tetrahydropyrimidines to the corresponding pyrimidines was attempted using several different techniques. Catalytic oxidation with ten percent palladium on charcoal produced small amounts of 2-phenyl-, 2-methyl-, and 2-aminopyrimidine from the corresponding tetrahydropyrimidine. Linstead's catalyst-d was used to dehydrogenate 2-phenyl, 2-methyl-, 2-amino-, and 2-mercaptopyrimidine, in yields ranging from less than five to 51 percent. Two quinones, chloranil and phenanthrenequinone, were studied as dehydrogenation agents. Small amounts of 2-phenyl- and 2-aminopyrimidine were prepared by treating the appropriate tetrahydropyrimidine with chloranil. Phenanthrenequinone proved completely unsuccessful. Sulfur was used to dehydrogenate 2-phenyl-1, 4, 5, 6-tetrahydropyrimidine and 2-amino-1, 4, 5, 6-tetrahydropyrimidine hydrochloride, again in only small yields. In reactions in which only a small amount of pyrimidine was obtained, ultraviolet spectroscopy was used for the identification of the pyrimidine. In general, none of the methods of dehydrogenation studied appeared to be useful as preparative techniques for pyrimidines.
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