Premium
9,9′‐Thiobis‐(1,2,3,4,7,8‐hexahydro‐7‐methyl‐6 H ‐pyrimido[1,6‐ a ]pyrimidine‐6,8‐dione)
Author(s) -
Šimo Ondrej,
Rybár Alfonz,
Alföldi Juraj,
Pätoprstý Vladimír
Publication year - 1999
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570360219
Subject(s) - thionyl chloride , chemistry , pyrimidine , derivative (finance) , medicinal chemistry , chloride , sulfur , organic chemistry , stereochemistry , financial economics , economics
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‐6 H ‐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‐6 H ‐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.