Document Detail


Effects of various bases on acid-catalyzed amination of 2-chloro-5-ethylpyrimidine: synthesis of PPARpan agonist GW693085.
MedLine Citation:
PMID:  20426493     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
A unique buffering effect of various bases, i-Pr(2)NEt and CaCO(3) in particular, was observed for the acid-catalyzed chloro displacement of 2-chloro-5-ethylpyrimidine with a 2-methyl-2-phenylpropanamine. The use of the carefully chosen bases was essential for the progression of the chloro displacement as well as the stability of the product in the presence of HCl formed. Research work leading to an efficient synthesis of PPARpan agonist GW693085 is described, featuring highly selective sequential N- and O-alkylations.
Authors:
Bobby N Glover; Lynda A Jones; Byron S Johnson; Alan Millar; Martin H Osterhout; Shiping Xie
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Publication Detail:
Type:  Journal Article    
Journal Detail:
Title:  The Journal of organic chemistry     Volume:  75     ISSN:  1520-6904     ISO Abbreviation:  J. Org. Chem.     Publication Date:  2010 Jun 
Date Detail:
Created Date:  2010-05-28     Completed Date:  2010-09-03     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  2985193R     Medline TA:  J Org Chem     Country:  United States    
Other Details:
Languages:  eng     Pagination:  3904-7     Citation Subset:  IM    
Affiliation:
Chemical Development, GlaxoSmithKline, Research Triangle Park, North Carolina 27709, USA.
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MeSH Terms
Descriptor/Qualifier:
Alkylation
Amination
Catalysis
Peroxisome Proliferator-Activated Receptors / agonists*
Pyrimidines / chemical synthesis*,  pharmacology
Chemical
Reg. No./Substance:
0/GW693085; 0/Peroxisome Proliferator-Activated Receptors; 0/Pyrimidines

From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine


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