Dimethylamination and Nitrosation of Pyrimidines with N-Nitrosodimethylamine

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Abstract

Reaction of a chloropyrimidine and a 5-activated pyrimidine in N-nitrosodimethylamine (NDA) resulted in the simultaneous formation of a dimethylaminopyrimidine and a 5-nitrosopyrimidine which is further transformed. A special type of Vilsmeier-Haack reaction using a mixture of NDA and phosphorus oxychloride (NDA+POCl3) for 5-activated pyrimidines has been accomplished. The reaction of 6-amino-1, 3-dimethyluracil with NDA+POCl3 under cooling gave bis (6-amino-1, 3-dimethyluracil-5-yl) methane, which was converted into 1, 3, 7, 9-tetramethyl (1H, 3H, 7H, 9H)-pyrido [2, 3-d, 6, 5-d'] dipyrimidine-2, 4, 6, 8-tetrone.

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