Diethyl bromomalonate → p-t-butyl-N-[6-chloro-5-(m-methoxyphenoxy)-4-pyrimidinyl]benzenesulfonamide

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Reaction Steps

Diethyl bromomalonate was converted with sodium m-methoxyphenolate in analogy to Example 1, paragraph c), into diethyl (m-methoxyphenoxy)malonate, colorless liquid. B.p. 143° C./0.05 Torr. The thus-obtained malonic ester was converted in analogy to Example 1, paragraph d), into 5-(m-methoxyphenoxy)-6-hydroxy-4(3H)-pyrimidinone from which in analogy to Example 1, paragraph e), there was prepared 4,6-dichloro-5-(m-methoxyphenoxy)pyrimidine, m.p. 109°-110° C. Reaction of the last-named compound with p-t-butylbenzenesulfonamide potassium yielded p-t-butyl-N-[6-chloro-5-(m-methoxyphenoxy)-4-pyrimidinyl]benzenesulfonamide, m.p. 152° C. (from methanol).

Provenance & Evidence