7038-67-7Relevant articles and documents
Chemoselective reactions of 4,6-dichloro-2-(methylsulfonyl)pyrimidine and related electrophiles with amines
Baiazitov, Ramil,Du, Wu,Lee, Chang-Sun,Hwang, Seongwoo,Almstead, Neil G.,Moon, Young-Choon
, p. 1764 - 1784 (2013/07/26)
Chemoselective SNAr reactions of 4,6-dichloro-2-(methylsulfonyl) pyrimidine and several related electrophiles with amines and their derivatives are described. In the presence of weak bases anilines and secondary aliphatic amines selectively displace the chloride group. Deprotonated anilines and their carbonyl derivatives displace the sulfone group. Sterically and electronically unbiased primary aliphatic amines selectively displace the sulfone group in 4,6-dichloro-2-(methylsulfonyl)pyrimidine; however, their reactions with other electrophiles generally are less selective. Steric-driven selectivity explanation was proposed. Georg Thieme Verlag Stuttgart. New York.
Novel antiallergic agents. Part I: Synthesis and pharmacology of pyrimidine amide derivatives
Ban, Masakazu,Taguchi, Hiroaki,Katsushima, Takeo,Aoki, Shoichi,Watanabe, Akihiko
, p. 1057 - 1067 (2007/10/03)
We have synthesized many pyrimidine amide derivatives. Novel pyrimidine bis-glycolic amide derivatives showed moderate inhibition in the rat passive cutaneous anaphylaxis (PCA) assay by oral administration. Among these compounds, 2,4-bis(methoxyacetylamino)-6-piperidinopyrirnidine (2i) exhibited significant inhibition. However the compound (2i) did not inhibit antigen-induced histamine or SRS-A release from lung fragments of the guinea-pig at less than 10-4 M. Derivatives of 2i have also notable or moderate activity in the rat PCA assay. Compound 2h which has no oxygen atom at the α-position of the amide carbonyl group and, compound 17 which has no amide carbonyl group, showed no inhibition in the rat PCA assay. We supposed that both the amide carbonyl group and the oxygen atom at α-position of the amide carbonyl group play an important role in inhibiting the rat PCA reaction. These pyrimidine bis-glycolic amide derivatives have a novel structure and unique activity which suggests they may be potentially useful in the treatment of allergic diseases. Copyright (C) 1998 Elsevier Science Ltd.