caa a22 4500 445878762 CHVBK 20180317145535.0 cr unu---uuuuu 170323e20111101xx s 000 0 eng 10.1007/s11030-011-9314-5 doi (NATIONALLICENCE)springer-10.1007/s11030-011-9314-5 Synthesis of highly substituted 2,3-dihydropyrimido[4,5- d ]pyrimidin-4(1 H )-ones from 4,6-dichloro-5-formylpyrimidine, amines and aldehydes [Elektronische Daten] [Jinbao Xiang, Chao Geng, Lang Yi, Qun Dang, Xu Bai] 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. Springer Science+Business Media B.V., 2011 2,3-dihydropyrimido[4,5- d ]pyrimidin-4(1 H )-ones nationallicence 4,6-dichloro-5-formylpyrimidine nationallicence Cyclization reaction nationallicence Intramolecular amide addition nationallicence Xiang Jinbao The Center for Combinatorial Chemistry and Drug Discovery, The School of Pharmaceutical Sciences and The College of Chemistry, Jilin University, 1266 Fujin Road, 130021, Changchun, Jilin, People's Republic of China aut Geng Chao The Center for Combinatorial Chemistry and Drug Discovery, The School of Pharmaceutical Sciences and The College of Chemistry, Jilin University, 1266 Fujin Road, 130021, Changchun, Jilin, People's Republic of China aut Yi Lang The Center for Combinatorial Chemistry and Drug Discovery, The School of Pharmaceutical Sciences and The College of Chemistry, Jilin University, 1266 Fujin Road, 130021, Changchun, Jilin, People's Republic of China aut Dang Qun The Center for Combinatorial Chemistry and Drug Discovery, The School of Pharmaceutical Sciences and The College of Chemistry, Jilin University, 1266 Fujin Road, 130021, Changchun, Jilin, People's Republic of China aut Bai Xu The Center for Combinatorial Chemistry and Drug Discovery, The School of Pharmaceutical Sciences and The College of Chemistry, Jilin University, 1266 Fujin Road, 130021, Changchun, Jilin, People's Republic of China aut Molecular Diversity Springer Netherlands 15/4(2011-11-01), 839-847 1381-1991 15:4<839 2011 15 11030 https://doi.org/10.1007/s11030-011-9314-5 text/html Onlinezugriff via DOI 1 research-article jats NATIONALLICENCE 856 40 https://doi.org/10.1007/s11030-011-9314-5 text/html Onlinezugriff via DOI NATIONALLICENCE 700 1- Xiang Jinbao The Center for Combinatorial Chemistry and Drug Discovery, The School of Pharmaceutical Sciences and The College of Chemistry, Jilin University, 1266 Fujin Road, 130021, Changchun, Jilin, People's Republic of China aut NATIONALLICENCE 700 1- Geng Chao The Center for Combinatorial Chemistry and Drug Discovery, The School of Pharmaceutical Sciences and The College of Chemistry, Jilin University, 1266 Fujin Road, 130021, Changchun, Jilin, People's Republic of China aut NATIONALLICENCE 700 1- Yi Lang The Center for Combinatorial Chemistry and Drug Discovery, The School of Pharmaceutical Sciences and The College of Chemistry, Jilin University, 1266 Fujin Road, 130021, Changchun, Jilin, People's Republic of China aut NATIONALLICENCE 700 1- Dang Qun The Center for Combinatorial Chemistry and Drug Discovery, The School of Pharmaceutical Sciences and The College of Chemistry, Jilin University, 1266 Fujin Road, 130021, Changchun, Jilin, People's Republic of China aut NATIONALLICENCE 700 1- Bai Xu The Center for Combinatorial Chemistry and Drug Discovery, The School of Pharmaceutical Sciences and The College of Chemistry, Jilin University, 1266 Fujin Road, 130021, Changchun, Jilin, People's Republic of China aut NATIONALLICENCE 773 0- Molecular Diversity Springer Netherlands 15/4(2011-11-01), 839-847 1381-1991 15:4<839 2011 15 11030 Metadata rights reserved Springer special CC-BY-NC licence nationallicence BK010053 XK010053 XK010000 NATIONALLICENCE NATIONALLICENCE NL-springer