The Development of Practical Synthetic Routes to a CB2 Agonist: Efficient Construction of a Densely Substituted Purine Core

An efficient and scalable process for the preparation of a purine-based CB2 agonist was developed. The production route to the requisite purine core relies on N-acylation and sequential substitution of a 5-amino-4,6-dichloropyrimidine with two amine building blocks followed by a cyclocondensation re...

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Bibliographic Details
Published inOrganic process research & development Vol. 17; no. 2; pp. 231 - 238
Main Authors DeBaillie, Amy C, Jones, Chauncey D, Laurila, Michael E, Magnus, Nicholas A, Staszak, Michael A
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 15.02.2013
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Applied
Chemistry, Organic
Physical Sciences
Science & Technology
RECEPTORS
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Summary:An efficient and scalable process for the preparation of a purine-based CB2 agonist was developed. The production route to the requisite purine core relies on N-acylation and sequential substitution of a 5-amino-4,6-dichloropyrimidine with two amine building blocks followed by a cyclocondensation reaction. The chemistry was successfully employed to rapidly prepare over 5 kg of the active pharmaceutical ingredient. To further improve efficiencies, postproduction development resulted in a rearranged synthesis which reduced the need for pressure reactors and introduced the most costly reagent in the final step.
ISSN:1083-6160
1520-586X
DOI:10.1021/op300278c