Efficient Synthesis of 4-Amino-2-methoxy-7,8-dihydropyrido[4,3-d]pyrimidin-5-ones: Practical Access to a Novel Chemotype in the Development of DGAT-1 Inhibitors

Abstract A practical access to an unprecedented, fused bicyclic 4-amino-2-alkoxy-7,8-dihydropyrido[4,3- d ]pyrimidin-5-one scaffold is developed. The synthesis of the potent inhibitor, 2-{4-[4-amino-2-methoxy-5-oxo-7,8-dihydropyrido[4,3- d ]pyrimidin-6(5 H )-yl]phenyl}-2-methylpropanamide is detaile...

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Published in:Synthesis (Stuttgart) 2012-10, Vol.44 (20), p.3152-3157
Main Authors: Bahnck, Kevin B., Shavnya, Andrei, Tao, Yong, Lilley, Susan C., Andrews, Melissa P., Aspnes, Gary E., Bernhardson, David J., Bill, David R., Bundesmann, Mark W., Dow, Robert L., Karki, Kapil, Le, Tung, Li, Qifang, Munchhof, Michael J., Nematalla, Asaad, Nihlawi, Mohammed, Patel, Leena, Perreault, Christian, Waldo, Michael
Format: Article
Language:English
Subjects:
Chemistry
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings
Organic chemistry
practical synthetic procedures
Preparations and properties
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Summary:Abstract A practical access to an unprecedented, fused bicyclic 4-amino-2-alkoxy-7,8-dihydropyrido[4,3- d ]pyrimidin-5-one scaffold is developed. The synthesis of the potent inhibitor, 2-{4-[4-amino-2-methoxy-5-oxo-7,8-dihydropyrido[4,3- d ]pyrimidin-6(5 H )-yl]phenyl}-2-methylpropanamide is detailed, with particular emphasis placed on synthetic efficiency and scalability. With the isolation of solid intermediates, the routes described offer clear elements of practicality and facilitate production of the target compound on large scale (>10 g) without chromatography.
ISSN:0039-7881
1437-210X
DOI:10.1055/s-0032-1316756