9,9′-Thiobis-(1,2,3,4,7,8-hexahydro-7-methyl-6H-pyrimido[1,6-a]pyrimidine-6,8-dione)

The 6‐(3‐hydroxypropylamino)‐3‐methylpyrimidine‐2,4‐dione (1) did not afford the expected 6‐(3‐chloro‐propylamino)‐ derivative on reaction with thionyl chloride, but, instead, the pyrimidine rings were joined via a sulfur bridge to give 9,9′‐thiobis(1,2,3,4,7,8‐hexahydro‐7‐melnyl‐6H‐pyrimido[1,6‐a]p...

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Bibliographic Details
Published in:Journal of heterocyclic chemistry 1999-03, Vol.36 (2), p.453-456
Main Authors: Šimo, Ondrej, Rybár, Alfonz, Alföldi, Juraj, Pätoprstý, Vladimír
Format: Article
Language:English
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Summary:The 6‐(3‐hydroxypropylamino)‐3‐methylpyrimidine‐2,4‐dione (1) did not afford the expected 6‐(3‐chloro‐propylamino)‐ derivative on reaction with thionyl chloride, but, instead, the pyrimidine rings were joined via a sulfur bridge to give 9,9′‐thiobis(1,2,3,4,7,8‐hexahydro‐7‐melnyl‐6H‐pyrimido[1,6‐a]pyrirnidine‐6,8‐dione) (3). An identical 9,9′‐thiobis‐ derivative 3 was obtained when reacting thionyl chloride with 1,2,3,4,7,8‐hexahydro‐7‐methyl‐6H‐pyrimido[1,6‐a]pyrimidine‐6,8‐dione (4). We suppose the sulfoxide‐ derivative 2 to be the intermediate of both routes: it underwent reduction to the final sulfide 3 in excess thionyl chloride.
ISSN:0022-152X
1943-5193
DOI:10.1002/jhet.5570360219