Abstract
Condensation-cyclization of 6-guanidinohexanoic acid (I) and chloromalonaldehyde in equimolar amounts in conc. sulfuric acid, by the application of chlorosulfonic acid under ice cooling, yielded 6-(5-chloro-2-pyrimidinyl) aminohexanoic acid (IV). Similar reaction with application of bromomalonaldehyde afforded the corresponding 5-bromo compound. Reaction of the hydrochloride of (I) and sodium nitromalonaldehyde in aqueous solution, with piperidine as a condensation agent, at room temperature yielded 6-(5-nitro-2-pyrimidinyl) aminohexanoic acid (VI), whose reduction with stannous chloride and hydrochloric acid gave the corresponding 5-amino compound (VII). Whereas (I) was resistant to esterification by the ordinary method, (VI) easily submitted to esterification. Fusion of a mixture of 2-methylthio-4, 6-dimethylpyrimidine (XI) and 6-aminohexanoic acid by heating to 200° in an oil bath afforded 6-(4, 6-dimethyl-2-pyrimidinyl) aminohexanoic acid. (XI) was prepared from acetylacetone and S-methylisothiourea according to the method of Hale and others. At the same time, some white needle crystals (X), m. p. 155.5-156°, were obtained as a by-product, whose analytical values corresponded to the formula of C7H10N4 and the substance was determined as 4, 6-dimethylpyrimidine-5-carbamidine by the synthesis of its derivatives.
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