An efficient route to 4-aryl-5-pyrimidinylimidazoles via sequential functionalization of 2,4-dichloropyrimidine.
[reaction: see text] Starting from 2,4-dichloropyrimidine, a concise synthetic route to medicinally important 4-aryl-5-pyrimidinylimidazoles is described. Sequential substitution of the 4- and 2-chloro groups using a regioselective Sonogashira coupling, followed by nucleophilic substitution, led to pyrimidinylalkyne derivatives, which were then oxidized to their corresponding 1,2-diketones. These 1,2-diketones, on cyclocondensation with ammonium acetate and an aldehyde, furnished the desired pyrimidinyl imidazoles in good overall yields.
Deng
Xiaohu
X
Johnson & Johnson Pharmaceutical Research & Development, LLC, San Diego, California 92121, USA.
Mani
Neelakandha S
NS
D002384:Catalysis; D006843:Hydrocarbons, Chlorinated / Q000737:chemistry*; D007093:Imidazoles / Q000138:chemical synthesis*; D015394:Molecular Structure; D011743:Pyrimidines / Q000138:chemical synthesis* / Q000737:chemistry*
D006843:Hydrocarbons, Chlorinated; D007093:Imidazoles; D011743:Pyrimidines; C513879:2,4-dichloropyrimidine