Selective addition of amines to 5-trifluoromethyl-2, 4-dichloropyrimidine induced by Lewis acids

DT Richter, JC Kath, MJ Luzzio, N Keene, MA Berliner…

Index: Richter, Daniel T.; Kath, John C.; Luzzio, Michael J.; Keene, Nandell; Berliner, Martin A.; Wessel, Matthew D. Tetrahedron Letters, 2013 , vol. 54, # 35 p. 4610 - 4612

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Citation Number: 4

Abstract

Abstract A variety of 2, 4-diamino-pyrimidine systems can be prepared from the corresponding 2, 4-dichloro-pyrimidine by sequential addition of two amines, the first adding selectively to the 4-position. In contrast it was found that 2, 4-dichloro-5-trifluoromethyl- pyrimidine yields a 1: 1 mixture of the two possible isomers. Lewis acids were employed to increase the ratio of isomers to> 10: 1 in favor of the 2-addition product. Optimization of the ...

~71%

Trifluoromethylpyrimidine-based inhibitors of proline-rich t...

[Walker, Daniel P.; Christopher Bi; Kalgutkar, Amit S.; Bauman, Jonathan N.; Zhao, Sabrina X.; Soglia, John R.; Aspnes, Gary E.; Kung, Daniel W.; Klug-McLeod, Jacquelyn; Zawistoski, Michael P.; McGlynn, Molly A.; Oliver, Robert; Dunn, Matthew; Li, Jian-Cheng; Richter, Daniel T.; Cooper, Beth A.; Kath, John C.; Hulford, Catherine A.; Autry, Christopher L.; Luzzio, Michael J.; Ung, Ethan J.; Roberts, W. Gregory; Bonnette, Peter C.; Buckbinder, Leonard; Mistry, Anil; Griffor, Matthew C.; Han, Seungil; Guzman-Perez, Angel Bioorganic and Medicinal Chemistry Letters, 2008 , vol. 18, # 23 p. 6071 - 6077]