title: Efficient preparation of 2,4-diaminopyrimidine nucleosides: total synthesis of lysidine and agmatidine.
abstract: An efficient route for the synthesis of 2,4-diaminopyrimidine ribosides from cytidine is described consisting of six steps with overall yields >50% and only one chromatographic step. The key amine addition step utilizes LiCl and 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) to ensure clean conversion to a single tautomeric product. This route has been used to prepare the modified tRNA nucleosides lysidine and agmatidine in quantities suitable for structural characterization.
authors: Pharmaceutical Sciences Division, School of Pharmacy, University of Wisconsin-Madison, Madison, Wisconsin 53705, United States.
authors: Brett J
authors: BJ
authors: Kopina
authors: Charles T
authors: CT
authors: Lauhon
mesh_terms: D003562:Cytidine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D008239:Lysine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D015394:Molecular Structure; D011741:Pyrimidine Nucleosides / Q000138:chemical synthesis* / Q000737:chemistry; D011743:Pyrimidines / Q000138:chemical synthesis* / Q000737:chemistry; D012313:RNA / Q000737:chemistry
chemical_list: D011741:Pyrimidine Nucleosides; D011743:Pyrimidines; C548874:agmatidine; C017205:2,4-diaminopyrimidine; D003562:Cytidine; D012313:RNA; C101421:lysidine; D008239:Lysine