Study on the reaction of methyl N-Methyl-N-(6-substituted-5-nitropyrimidin-4-yl)glycinates with sodium alkoxides

✍ Scribed by Inga Susvilo; Algirdas Brukstus; Sigitas Tumkevicius

• Book ID: 102892011
• Publisher: Journal of Heterocyclic Chemistry
• Year: 2006
• Tongue: English
• Weight: 845 KB
• Volume: 43
• Category: Article
• ISSN: 0022-152X
• DOI: 10.1002/jhet.5570430205

✦ Synopsis

Methyl N-methyl-N- (6-substituted-5-nitropyrimidin-4-yl)glycinates (4a-n), obtained from 6-substituted-4-chloro-5-nitropyrimidines and sarcosine methyl ester (methyl 2-(methylamino)acetate), in the reaction with sodium alkoxides underwent transformations to give different products. N-methyl-N-(5nitropyrimidin-4-yl)glycinates (4a,i,j) bearing amino and arylamino groups in the position 6 of the pyrimidine ring gave corresponding 6-substituted-4-methylamino-5-nitrosopyrimidines (5a,i,j). In the reaction of N-(6-alkylamino-5-nitropyrimidin-4-yl)-N-methylglycinates (4b,f-h) with sodium alkoxides the corresponding 6-alkylamino-4-methylamino-5-nitrosopyrimidines (5b,f-h) and 5-hydroxy-8-methyl-5,8dihydropteridine-6,7-diones (6b,f-h) were formed. The main products of the reaction of N-(6dialkylamino-5-nitropyrimidin-4-yl)-N-methylglycinates (4c-e,k,l), after work-up, were the corresponding 6-dialkylamino-9-methylpurin-8-ones (7c-e,k,l) and 8-alkoxy-6-dialkylamino-9-methylpurines (9c,l, 10c,l). thio]-5-nitropyrimidin-4-yl}glycinate (4n) under the same conditions gave methyl 7-methylaminothiazolo [5,4-d]pyrimidine-2-carboxylate (13). Mechanisms of the observed transformations are discussed.