1. Pd-catalysed amidation of 2,6-dihalopurine nucleosides. Replacement of iodine at 0 ºC
- Author
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Jaume Vilarrasa, Montserrat Terrazas, Lluís Bosch, Joaquim Caner, Ionela Cialicu, Anna M. Costa, Xavier Ariza, and Universitat de Barcelona
- Subjects
Compostos heterocíclics ,Chemistry ,Xantphos ,Organic Chemistry ,Chlorine atom ,Àcids nucleics ,Substituent ,chemistry.chemical_element ,Nucleosides ,Iodine ,Biochemistry ,Medicinal chemistry ,Toluene ,Medicaments antineoplàstics ,Citotoxicitat per mediació cel·lular ,Nucleic acids ,Cell-mediated cytotoxicity ,chemistry.chemical_compound ,Nucleòsids ,Drug Discovery ,Antineoplastic agents ,Reactivity (chemistry) ,Heterocyclic compounds ,Benzamide ,Nucleoside - Abstract
Pd-catalysed reactions of 2-Cl, 2-Br and 2-I derivatives of a 6-chloropurine nucleoside with benzamide have been compared, using Pd 2 dba 3 , Xantphos and Cs 2 CO 3 in toluene, between 20 and 80!C. The reactivity order was 2-I > 2-Br > 6-Cl!2-Cl. The 2-I substituent could be replaced even at 0!C, under conditions disclosed here for the first time. On the other hand, the replacement of the chlorine atom at position 2 (2Cl) required 110!C.
- Published
- 2012