Synthesis of pyrazolo[1,5-alpha]pyrimidinone regioisomers.

Autor: Gavrin LK; Department of Exploratory Medicinal Chemistry and Chemical Technologies, Wyeth Research, 200 CambridgePark Drive, Cambridge, Massachusetts 02140, USA. gavrinl@wyeth.com, Lee A, Provencher BA, Massefski WW, Huhn SD, Ciszewski GM, Cole DC, McKew JC
Jazyk: angličtina
Zdroj: The Journal of organic chemistry [J Org Chem] 2007 Feb 02; Vol. 72 (3), pp. 1043-6.
DOI: 10.1021/jo062120g
Abstrakt: This work describes two distinct routes to prepare pyrazolo[1,5-alpha]pyrimidin-7-ones and two distinct routes to prepare pyrazolo[1,5-alpha]pyrimidin-5-ones. Use of 1,3-dimethyluracil as the electrophile in the preparation of the pyrimidin-5-one regioisomer represents a correction of previously reported results. Also, a novel reaction to prepare this isomer was identified and the reaction mechanism elucidated. This work provides the experimentalist with complimentary synthetic pathways that afford either the pyrimidin-7-one or the pyrimidin-5-one regioisomer.
Databáze: MEDLINE