Studies on Antitumor Substances. VII. Reaction of N-Amidino-O-alkylisourea with Some Carboxylic Esters

Abstract

The reaction of N-amidino-O-alkylisourea with some carboxylic esters was attempted. Condensation with diethyl oxalate in alcohol gave alkyl 4-amino-6-alkoxy-s-triazine-2-carboxylate through the formation of the five membered-ring intermediate. Alkyl 4-amino-6-alkoxy-s-triazine-2-carboxylate was easily converted into the coresponding amide with a variety of amines. Condensation with ethyl acetoacetate gave 6-methyl-2-alkoxyamidino-4-pyrimidinol and 4-amino-2-alkoxy-6-acetomethyl-s-triazine. Condensation with ethyl cyanoacetate afforded only 4-amino-2-alkoxy-6-cyanomethyl-s-triazine, but not any expected pyrimidinol. Condensation with ethyl chloroacetate gave 4-amino-2-alkoxy-6-chloromethyl-s-triazine, which was converted into 4-amino-2-alkoxy-6-substituted amino-s-triazine with a variety of amines.