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2,4,6‐trichloropyrimidine. Reaction with anilines
Author(s) -
Schomaker Jennifer M.,
Delia Thomas J.
Publication year - 2000
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.5570370609
Subject(s) - chemistry , aniline , solvent , ring (chemistry) , ethanol , medicinal chemistry , organic chemistry
The reaction of 2,4,6‐trichloropyrimidine 1 with a variety of 4‐substituted anilines 2 has been investigated. Monosubstitution occurs readily for all anilines except those containing strongly electron‐withdrawing groups. The yields of the isomeric products 3 and 4 parallel the Hammet constants of the ring substituents. The main product when ethanol was used as the solvent was the 4‐substituted‐2,6‐dichloropyrimidine 3. Spectral and X‐ray data confirmed this assignment. However, a solvent dependence on the 3:4 ratio was demonstrated. In some cases, excess aniline under forcing conditions led to 2,4‐disubstituted products.