Process research and development of a dihydropyrimidine dehydrogenase inactivator: Large-scale preparation of eniluracil using a Sonogashira coupling

…, R Bright, MJ Coleman, KP Jenkins

Index: Cooke, Jason W. B.; Bright, Robert; Coleman, Mark J.; Jenkins, Kevin P. Organic Process Research and Development, 2001 , vol. 5, # 4 p. 383 - 386

Full Text: HTML

Citation Number: 49

Abstract

Eniluracil (5-ethynyluracil) is a potent inactivator of the enzyme dihydropyrimidine dehydrogenase, which is the rate-limiting enzyme in the metabolism of 5-fluorouracil, a widely used anti-cancer drug. The process research and development of a three-stage route to eniluracil is described. A Sonogashira coupling between 5-iodouracil and trimethylsilylacetylene was used to synthesise 5-(2-trimethylsilylethynyl) uracil on a> 60 kg ...