A cascade reaction sequence en route to 7-substituted 2-aminopyrrolo[1,2-a]pyrimidine-4,6-diones and the corresponding acrylic acid derivatives

ORGN 740

Ju Gao, ju.gao@abbott.com and Andrew J Souers, andrew.souers@abbott.com. Metabolic Disease Research, Abbott Laboratories, Global Pharmaceutical Research Division, 100 Abbott Park Road, Abbott Park, IL 60064-6101
Reaction of a-bromo ketones with 6-amino-2-methylpyrimidin-4(3H)-one under basic conditions and in the presence of atmospheric oxygen affords novel 7-substituted 2-amino-pyrrolo[1,2-a]pyrimidine-4,6-diones that are readily hydrolyzed to afford the corresponding acrylic acid derivatives. The reaction sequence consists of an initial alkylation, followed by an unexpected condensation, elimination, and oxidation sequence to afford the products. This cascade reaction sequence represents an unprecedented route to the described products.

 

 

Combinatorial, Parallel and Process Chemistry, Heterocycles, Aromatics, New Reactions and Methodology
8:00 PM-10:00 PM, Wednesday, August 22, 2007 BCEC -- Exhibit Hall - B2, Poster

Division of Organic Chemistry

The 234th ACS National Meeting, Boston, MA, August 19-23, 2007