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Communication | Regular issue | Vol 55, No. 3, 2001, pp.439-446
Published online, 1st January, 1970
DOI: 10.3987/COM-00-9126
Unsymmetrical 4,6-Diamino-2-methyl-5-nitropyrimidine Synthesis via 4,6-Bis(tosylates)

Gary A. Cain* and James P. Beck

*Experimental Station E336/109, Chemical and Physical Sciences Department, DuPont Pharmaceuticals Company, P.O.Box 80336, Wilmington, DE 19880-0336, U.S.A.


Chlorides have traditionally been used as leaving groups for the introduction of 4- and 6-heteroatomic substituents onto pyrimidines. Use of 4,6-dichloro-2-methyl-5-nitropyrimidine allows the sequential introduction of different 4- and 6-heteroatomic substituents onto this core; however, this reagent is highly hazardous to handle. We have found that the analogous 4,6-bis(tosylate) offers a less hazardous substance which undergoes the same nucleophilic aromatic substitution chemistry as the dichloride, including sequential introduction of different nucleophiles.