Reactions of Monosubstituted Guanidines with 1-Phenyl-1-butane-1,3-dione

Article abstract of DOI:10.1007/BF00798647

Methyl-, benzyl- and phenylguanidine (2b-d) react with 1-phenyl-1,3-butanedione to yield exclusively N²-substituted 4-methyl-6-phenyl-2-pyrimidinamines 10b-d.The formation of isomeric N¹-substituted 2(1H)-pyrimidinimines 11 or 12 cannot be observed.The structural formulae of 10b and c were proved by spectroscopical methods.The structure of the phenylguanidine-phenylbutanedione-condensate was determined by comparison and establishment of the identity of its picrate with an authentical sample of 10d-picrate, which had been synthetized from pyrimidinthione 13 (via methylthiopyrimidine 16*HCl).Boiling 13 with aniline in butanol yields thiodipyrimidine 15 (and not 10d). - (Keywords: 1,3-Butanedione, 1-phenyl, reactions with monosubstituted guanidines; β-Diketones, reactions with monosubstituted guanidines; Guanidines, monosubstituted, reactions with 1-phenyl-1,3-butanedione; Pyridmidine, 4-methyl-2-methylthio-6-phenyl, hydroiodide; 2-Pyrimidine-amines, 4-methyl-6-phenyl-N²-substituted, and salts; 2,2'-Thiodipyrimidine, 4,4'-dimethyl-6,6'-diphenyl)