Herein, we report the synthesis and the use of new N-1-dinitrophenyi-inosine based solid supports, in which the C-2 of the purine base is strongly activated toward the attack of N-nucleophiles. The synthesized supports, binding the nucleoside by a 5'-O-monomethoxytrityl function, have been used to accomplish the synthesis of a small library of N-1 alkylated inosine and AICAR derivatives. In addition, cleavage of the 2'-3' ribose bond of N-1 alkylated inosine derivatives anchored to the supports allowed to prepare a new set of N-1 alkylated-2',3'-secoinosine derivatives in high yields. (c) 2006 Elsevier Ltd. All rights reserved.