Tetrahedron Letters,Vo1.30,No.20,pp 2669-2672,1989 0040-4039/89 $3.00 + -00 Printed in Great Britain Pergamon Press plc OH THE RRACTICM zyxwvutsrqponmlkjihgfedcbaZYXWVUTSRQPONMLKJIHGFEDCBA OF 6-GLm 5-NITROSOPYRWDIWS UITHVILSMRfER-TTPR REAGENTS. z3YPmmsIsoF8-ucIlso-9-oLycosyLrmBIAEs M. MELGUIZO, M. NOGUERAS, A. SANCHEZ and Me L. QUIJANO Department of Organic Chemistry. University College of JaBn. University of Granada. 23071-Ja&?. Spain Summary: S-amino, B-(N-methyl)amino and 8-(N,N-dimethyljamino-9-glucopyranosylpurines have been obtained by reaction of the corresponding 6-glycopyranosyl-5-nitrosopyrimidine with Vilsmeier-Type reagents (formamide, substituted formamides and phosphorus oxychloride). Studies on reactivity and synthetic applications of several 6-glycosylaminopyrimidi- nes have been carried out 1,2,3 . Our interest is focused on the preparation of derivatives with potential biological activity. We report herein the utility of 6-glycosylamino-5 nitrosopyrimidines for the synthesis of as shown in the scheme. B-amino(N-methylamino and N,N-dimethylaminojpurines The Vilsmeier-Type reagents (Vilsmeier-Haack or Vilsmeier-Haack-Arnold) provide a very convenient method for the cyclisation in the carbocyclic com- pounds chemistry as well as in the heterocyclic 4 compounds . Furthermore, Vilsmeier reaction exhibits a large dependence on the conditions under which it takes place such as concentration and temperature5. We have used this reaction for the formylation of some 6-glycosylaminopyrimidines with excellent yield'. K. Senga and coworker have obtained 8-(N-methyl) and 8-(N.N-dimethyl)aminopurinesby treatment of 6-amino-%nitrosopyrimidines with substituted formamides and phosphorus oxychloride in equimolar amounts at high 7 temperature . When the reaction was carried out with 6-amino-1.3-dimethyl-5-nitroso zyxwvutsrqponmlkjihgfedcbaZYXWVUTSRQPONMLKJIH urac ile at room temperature, a dimeric compound was obtained which converted into the corresponding 8-(N,N-dimethyl)aminopurine by futher heating in the same reagent or by sublimating "in vacua". Nevertheless, 8-aminopurines were not obtained when the reaction was carried out with formamide; instead, the formation of 8 small amounta of pyrimido[4,5_d]pyrimidines was observed in these cases . In this letter, we present the results of our study on the reactionsof 3,4-dihydro- 2669