A study of the permanganate oxidation of 4-methylpyrimidine to pyrimidine-4-carboxylic acid Public Deposited

http://ir.library.oregonstate.edu/concern/graduate_thesis_or_dissertations/r781wj36c

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  • The yields from the oxidation of 4-methylpyrimidine with potassium permanganate were found to increase from 25 to 92 percent by the addition of small amount of potassium hydroxide to the reaction mixture. Pyrimidine-4-carboxylic acid decarboxylates in hot aqueous solution to yield pyrimidine and carbon dioxide. The rate is that decarboxylation is markedly effected by the alkalinity of the solution. No unreacted 4-methylpyrimidine survived the permanganate oxidation as reported by Gabriel, Several derivatives of pyrimidine-4-carboxylic acid were prepared. The pyrimidine-4-carboxylic acid was found to be water soluble only to the extent of one part in 300 at room temperature but fairly soluble at elevated temperature. The ionization constant of the acid was found to be 6.1 x 10[superscript -]⁴. 4-Methylpyrimidine is best prepared by the one-step operation involving the condensation of 4, 4-dimethyoxy-2-butanone and formamide as reported by Bredereck, Gompper and Morlock. 2, 6-Dichlo-4-methylpyrimidine was found to be so unstable as to be unsuitable for synthetic work even when at deepfreeze temperatures over period of several days.
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