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Synthesis of a novel, recyclable, solid-phase acylating reagent.
Robert B Nicewonger1, Lori Ditto, Doug Kerr
1Department of Chemistry ArQule, Inc., 19 Presidential Way, Woburn, MA 01801, USA. rnicewonger@arqule.com
Bioorganic & Medicinal Chemistry Letters
|June 28, 2002
Summary
This study details the synthesis of novel pyridinopyrimidine imides using conventional and microwave methods. The immobilized imide demonstrated comparable efficacy to solution-phase counterparts in amine acylation reactions.
Area of Science:
- Organic Chemistry
- Medicinal Chemistry
- Synthetic Chemistry
Background:
- Pyridinopyrimidine derivatives are important scaffolds in medicinal chemistry.
- Developing efficient synthetic routes for functionalized heterocycles is crucial.
- Immobilized reagents offer advantages in purification and reusability.
Purpose of the Study:
- To synthesize novel N-(6-cyano-1,3-dimethyl-2,4-dioxo-5-substituted-1,3-dihydropyridino[2,3-d] pyrimidin-7-yl)imides.
- To investigate the efficacy of conventional heating and microwave-assisted synthesis.
- To explore the application of immobilized imides in acylation reactions.
Main Methods:
- Synthesis of pyridinopyrimidine imides via conventional heating.
- Microwave-assisted synthesis of pyridinopyrimidine imides.
- Immobilization of the synthesized imide onto polystyrene support.
- Acylation of primary and secondary amines using both solution-phase and immobilized imides.
Main Results:
- Successful synthesis of target pyridinopyrimidine imides.
- Microwave irradiation accelerated the synthesis compared to conventional heating.
- The immobilized imide exhibited comparable or superior reactivity in amine acylation.
- Facilitated purification and potential for reagent recovery with the immobilized system.
Conclusions:
- Efficient synthetic strategies for novel pyridinopyrimidine imides were established.
- Microwave synthesis offers a time-efficient alternative.
- Immobilization of the imide provides a practical approach for amine acylation with benefits in purification and potential recycling.