Journal
MOLECULAR DIVERSITY
Volume 15, Issue 4, Pages 839-847Publisher
SPRINGER
DOI: 10.1007/s11030-011-9314-5
Keywords
2,3-dihydropyrimido[4,5-d]pyrimidin-4(1H)-ones; 4,6-dichloro-5-formylpyrimidine; Cyclization reaction; Intramolecular amide addition
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Funding
- National Natural Science Foundation of China [90713008]
- National Science & Technology Major Project Key New Drug Creation and Manufacturing Program of China [2009ZX09501-010]
- Changchun Discovery Sciences, Ltd.
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A practical strategy was developed for the preparation of highly substituted 2,3-dihydropyrimido[4,5-d]pyrimidin-4(1H)-ones from 4,6-dichloro-5-formylpyrimidine, primary amines, and aldehydes. The key step for this synthesis entails a cyclization reaction involving an intramolecular amide addition to an iminium intermediate formed in situ from 4-amino-pyrimidine-5-carboxamide 2 and aldehydes to form the pyrimido[4,5-d]pyrimidine core with a strategically placed 5-Cl group for further derivatization. The utility of this methodology was demonstrated through the preparation of a 27-membered library of representative 2,3-dihydropyrimido[4,5-d]pyrimidin-4(1H)-ones in moderate to good yields.
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