Synfacts 2007(9): 0996-0996  
DOI: 10.1055/s-2007-968925
Polymer-Supported Synthesis
© Georg Thieme Verlag Stuttgart · New York

An Efficient Solid-Phase Synthesis of Ureas

Contributor(s): Yasuhiro Uozumi, Yohei Oe
Y. Bolshan, M. J. Tomaszewski, V. Santhakumar*
AstraZeneca R&D Montréal, Canada
Further Information

Publication History

Publication Date:
23 August 2007 (online)

Significance

An efficient and simple solid-phase synthesis of ureas was described. Thus, treatment of carboxylic acids 1 with diphenyl phosphoryl azide (DPPA) in the presence of triethylamine at r.t., followed by addition of silica-bound thiol 2 and heating overnight gave the silica-bound thiocarbamate 3. The resulting thiocarbamate 3 reacted with amines 4 in acetonitrile to release the corresponding ureas 5 from the silica support in 45-98% yield.