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Traceless solid-phase synthesis of 2,4,6-chlorodiamino and triaminopyrimidines

✍ Scribed by Dario Montebugnoli; Pierfrancesco Bravo; Elisabetta Brenna; Charles Mioskowski; Walter Panzeri; Fiorenza Viani; Alessandro Volonterio; Alain Wagner; Matteo Zanda

Book ID: 104205655
Publisher: Elsevier Science
Year: 2003
Tongue: French
Weight: 404 KB
Volume: 59
Category: Article
ISSN: 0040-4020
DOI: 10.1016/s0040-4020(03)01097-4

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✦ Synopsis

An effective traceless solid-phase synthesis of chloro-diaminopyrimidines via an amino-de-chlorination reaction of polymerbound 4-alkoxycarbonylamino-2,6-dichloropyrimidines has been developed. After release from the polymer the target molecules were obtained in good to excellent purity, although with modest regiocontrol. Further reaction of solid-supported N-alkoxycarbonyl-chlorodiaminopyrimidines with secondary amines afforded triaminopyrimidines in good purity under mild conditions, whereas less nucleophilic primary amines did not perform well under the conditions explored so far.

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