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Controlling substitution patterns on the 1,2,4‐triazolo[1,5‐α]‐pyrimidine ring. Selective removal of chlorine at the 7‐position
Author(s) -
Monte William T.,
Kleschick William A.,
Bordner Jon
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.5570360127
Subject(s) - chemistry , pyrimidine , chlorine , ring (chemistry) , acetic acid , tetrahydrofuran , methanol , zinc , substitution (logic) , substrate (aquarium) , combinatorial chemistry , chlorine atom , copper , organic chemistry , medicinal chemistry , stereochemistry , oceanography , solvent , computer science , programming language , geology
A highly effective method for the selective removal of chlorine from the 7‐position of the 1,2,4‐triazolo[1,5‐α]pyrimidine ring in the presence of chlorine at the 5‐ or 6‐positions is reported. The method involves treatment of the appropriate substrate with zinc‐copper couple in the presence of acetic acid in methanol‐tetrahydrofuran. The method enables the construction of a variety of substitution patterns in key intermediates for the 1,2,4‐triazolo[1,5‐α]pyrimidine sulfonanilide herbicides.