A study of certain novel reactions of 4,6-dimethoxy-5-nitropyrimidine Public Deposited

http://ir.library.oregonstate.edu/concern/graduate_thesis_or_dissertations/tm70mz90v

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  • Reaction of 4, 6-dimethoxy-5-nitropyrimidine [I], with refluxing pyridine, was discovered to yield the methylpyridinium salt of 1, 6-dihydr -4-hydroxy-1-methyl-5-nitro-6-oxopyrimidine [III]. Possible use of I as a general N-methylating agent was explored. No appreciable reaction occurred between I and refluxing excess n-butyl alcohol. Similar reaction involving quinoline failed to yield an isolable quinolinium salt although the reaction gave an oily product. Equimolar amounts of I and pyridine in refluxing ethanol solvent gave no evidence of a reaction. As a means of minimizing isolation problems, equimolar amounts of I and pyridine without solvent were reacted. Under these conditions a second product resulting from rearrangement of I, 1, 6-dihydro-4-methoxy-l-methyl-5-nitro-6-oxopyrimidine [V] was isolated in addition to III. Fusion of I with equimolar amounts of piperidine, quinoline, and 4-methylpyrimidine, resulted in smaller amounts of V, and a black foamy solid, with no detectable methylation of the solvent.
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