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Studies on the syntheses of sulfur containing pyrimido 5 4 d pyrimidine derivatives part 2 syntheses and rearrangement of 2 methylsulfonyl pyrimido 5 4 d pyrimidine 6 sulfonamide derivatives



Studies on the syntheses of sulfur containing pyrimido 5 4 d pyrimidine derivatives part 2 syntheses and rearrangement of 2 methylsulfonyl pyrimido 5 4 d pyrimidine 6 sulfonamide derivatives



Yakugaku Zasshi 96(5): 586-592



In order to examine the relation between the structure and the activity of coronary vasodilation and inhibition of platelet aggregation [in dogs], 9 kinds of 2-methylsulfonylpyrimido-[5,4-d]pyrimidine derivatives possessing a sulfonamide group at the 6-position were synthesized. Reaction of N,N-bis(2-hydroxyethyl)-2-methylsulfonyl-4,8-dipiperidinopyrimido-[5,4-d]pyrimidine-6-sulfonamide (Va) with an excess of NaOH solution or an excess of diethanolamine at low temperature gave 6-[2-(2-hydroxyethylamino)ethoxy]-2-methylsulfonyl-4,8-dipiperidinopyrimido[5,4-d]pyrimidine (VIIa) in quantitative yield. When a mixture of Va and triethylamine was refluxed in butanol, 6-[bis(2-hydroxyethyl)-amino]-2-methylsulfonyl-4,8-dipiperidinopyrimido[5,4-d]pyrimidine (IXa) was obtained in good yield, and IXa was obtained by heating VIIa in butanol. Analogous sulfonamide derivatives also underwent a similar reaction.

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