618863-11-9Relevant academic research and scientific papers
Utility of 4,6-dichloro-2-(methylthio)-5-nitropyrimidine. Part 2: Solution phase synthesis of tetrasubstituted purines
Hammarstr?m, Lars G.J.,Meyer, Michael E.,Smith, David B.,Talamás, Francisco X.
, p. 8361 - 8363 (2003)
A simple synthesis of tetrasubstituted purines is disclosed based on the solution phase elaboration of 4,6-dichloro-2-methylthio-5-nitropyrimidine. One-pot sequential C4 and C6 chloride substitution by secondary and primary amines yields 4,6-diamino-2-methylthio-5-nitropyrimidines. mCPBA-mediated oxidation of the methylthio moiety to the corresponding sulfone allows facile substitution at the 2-position. CrCl2 assisted reduction of the nitro group, followed by acid catalyzed orthoester cyclization, then provides novel tetrasubstituted purines not accessible by other methods.
