Microwave-assisted intramolecular hetero Diels-Alder cycloaddition reaction of an acetylene-tethered pyrimidine

ORGN 624

Bin Shao, Discovery Research, Discovery Research, Purdue Pharma, L.P, 6 Cedar Brook Drive, Cranbury, NJ 08512
Intramolecular hetero Diels-Alder cycloaddition of a series of acetylene-tethered pyrimidines were accelerated under microwave irradiation. Generally, such conditions gave much cleaner products and higher isolated yields were obtained compared with conventional heating. In some cases that gave no products upon conventional heating, the present microwave assisted condition gave good to excellent yield of products. Based on the electronic character of the substituents on the pyrimidine, the cyclization reaction also shows chemical selectivity towards different diene moieties present in the pyrimidine structure.