Single-step synthesis of pyrimidine derivatives.
We describe a single-step conversion of various N-vinyl and N-aryl amides to the corresponding pyrimidine and quinazoline derivatives, respectively. The process involves amide activation with 2-chloropyridine and trifluoromethanesulfonic anhydride followed by nitrile addition into the reactive intermediate and cycloisomerization. In situ nitrile generation from primary amides allows for their use as nitrile surrogates. The use of this chemistry with sensitive N-vinyl amides and epimerizable substrates in addition to a wide range of functional groups is noteworthy.
Movassaghi
Mohammad
M
Massachusetts Institute of Technology, Department of Chemistry, Cambridge, Massachusetts 02139, USA. movassag@mit.edu
Hill
Matthew D
MD
D000577:Amides / Q000737:chemistry; D002626:Chemistry, Pharmaceutical / Q000379:methods*; D009682:Magnetic Resonance Spectroscopy; D008956:Models, Chemical; D009570:Nitriles / Q000737:chemistry; D011743:Pyrimidines / Q000138:chemical synthesis*; D013237:Stereoisomerism
D000577:Amides; D009570:Nitriles; D011743:Pyrimidines; C030986:pyrimidine