A complementary route to diaminopyrimidines through regioselective SNAr amination reactions

作者：O'Donnell Michael; Charrier Jean Damien^*

来源：Tetrahedron, 2015, 71(10): 1515-1522.

DOI：10.1016/j.tet.2015.01.043

• Diaminopyrimidines
• Nucleophilic aromatic substitution
• Regioselectivity
• Tetrafluorophenoxy

A novel approach towards the production of diverse sets of diaminopyrimidines through sequential SNAr reactions is reported. The readily prepared 2-chloro-4-tetrafluorophenoxypyrymidine reacts regioselectively with amines at the C-2 position. The tetrafluorophenoxy at C-4 can then be replaced with amines in a second SNAr to afford easy access to a different and complementary set of diaminopyrimidines. The broad utility of this 'C-2 then C-4' two-step sequence has been demonstrated with a range of aromatic and aliphatic amines.

• 出版日期2015-3-11