One-Pot Protocol for N-Alkylation of Purine, Pyrimidine and Azole Derivatives via Alcohols Using Ph3P/I2: Simple Route for Carboacyclic Nucleoside Synthesis.

Abstract A simple and efficient synthetic protocol for the one-pot N-alkylation of nucleobases and their related N-heterocycles via alcohols utilizing the combination of PPh 3 and I 2 is reported. In this protocol purine, pyrimidine and azole derivatives underwent the N-alkylation reaction with diverse primary alcohols using Ph 3 P/I 2 in the presence of Et 3 N-K 2 CO 3 in anhydrous DMF to give the N -alkyl adducts (carboacyclic nucleosides) in good yields (up to 90%). The influence of some parameters in this reaction including type of solvent, base, reagents and temperature was discussed. In addition, this protocol has proved the favorable selectivity towards primary hydroxyl versus secondary hydroxyl group in diols.