McCauley JA, Theberge CR, Liverton NJ
Department of Medicinal Chemistry, Merck Research Laboratories, West Point, Pennsylvania 19486, USA.
Org Lett. 2000 Oct 19;2(21):3389-91. doi: 10.1021/ol006499j.
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.
已证明碱对脒与取代的3-苯基-2-丙炔腈反应的化学选择性具有显著影响。脒1可与氰基炔2加成，以高选择性生成亚氨基嘧啶异构体3。加入2当量的NaHMDS会完全逆转反应的选择性，几乎 exclusively生成异构体4。该方法已用于制备多种取代的4-亚氨基嘧啶。
