The Reactivity of Related 6-Amino- and 5,6-Diaminouracils Derived from 2-Amino-5-(phenoxymethyl)-2-oxazoline: Efficient Access to Bicyclic Pyrimidine Derivatives

Abstract

8-(Dimethylamino)-3-(2-hydroxy-3-phenoxypropyl)xanthine has been obtained from 6-amino-1-(2-hydroxy-3-phenoxypropyl)uracil by an azodicarboxylate Michael-type addition involving a reactive diene. 6-Amino-1-(2-hydroxy-3-phenoxypropyl)uracil was easily prepared from racemic 2-amino-5-(phenoxymethyl)-2-oxazoline. Moreover, these chemical investigations also led to the identification of a racemic 7-aminooxazolo[5,4-d]pyrimidin-5(6H)-one, obtained by the condensation reaction of the phosgeniminium chloride, Viehe's salt, with 5,6-diamino-1-(2-hydroxy-3-phenoxypropyl)uracil.