Demethylation reactions of 4??amino??N??(2, 6??dimethoxy??4??pyrimidinyl) benzenesulfonamide (sulfadimethoxine) in strongly basic aqueous solution

…, A Yoshida, M Kato, T Yoshioka, H Tachi…

Index: Miura; Ono; Yoshida; Kato; Yoshioka; Tachi; Eguchi Journal of Heterocyclic Chemistry, 1994 , vol. 31, # 6 p. 1407 - 1411

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Abstract

Abstract Hydrolysis of 1 in strongly basic aqueous solution afforded mono-and didemethylated products 2, 3 and 4, that are postulated as the metabolites of 1 in some animals. This hydrolytic demethylation was shown to proceed stepwise via mono- demethylation to give 2 and 3, followed by their further demethylation to 4. The hydrolytic reactivity of 1–3 was rationalized based on MO calculation results and 13 C nmr data.