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Final Activity Report Summary - COMBICHEM-GIRONA (Synthesis of pyrimidine and spiroimidazolidinone libraries by combinatorial chemistry)

In this project, an efficient methodology has been developed for the synthesis of novel pyrimidines substituted at position 2 and / or 4 with an amino acid residue. We incorpored N-Boc-amino esters with an amine, hydroxyl, heteroaryl or phenol group in the side-chain at 2 position of the pyrimidine ring by nucleophilic displacement of a sulphone function. Two different strategies based on Mitsunobu and Petasis reaction were performed to introduce an amino ester residue at 4 position of the pyrimidine ring.

On the other hand, we set up a methodology for the rapid and efficient solid-phase synthesis of spiroimidazolidinones, in particular, of novel 1,4,8-triazaspiro[4.5]decan-2-one derivatives. We optimised the preparation of 1,4,8-triazaspiro[4.5]decan-2-one-1-acetamides substituted at 4 and 8 positions as well as the preparation of 4-aryl-8-benzyl-1,4,8-triazaspiro[4.5]decan-2-ones substituted at position 1. Both optimization studies were performed by the Multipin technology using SynphaseTM Lanterns as solid support. This methodology was used for the preparation of a collection of novel spiroimidazolidinone derivatives.

Reported by

UNIVERSITAT DE GIRONA
Campus de Montilivi
17071 GIRONA
Spain
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