title: Chemoselective reactions of amidines: selective formation of iminopyrimidine regioisomers
abstract: The dramatic effect of base on the chemoselectivity of the reaction of amidines with substituted 3-phenyl-2-propynylnitriles is demonstrated. Amidine 1 can be added to cyanoalkyne 2 to give iminopyrimidine isomer 3 with high selectivity. The addition of 2 equiv of NaHMDS completely reverses the selectivity of the reaction, yielding isomer 4 almost exclusively. This method has been used to prepare a variety of substituted 4-iminopyrimidines.
authors.affiliation: Department of Medicinal Chemistry, Merck Research Laboratories, West Point, Pennsylvania 19486, USA.
authors.initials: JA
authors.lastname: McCauley
authors.initials: CR
authors.lastname: Theberge
authors.initials: NJ
authors.lastname: Liverton