It has been found that the amination of 4-bromo-2,6-diphenylpyrimidine into the corresponding 4-amino compound with potassium amide in liquid ammonia at -33" does not occur by the ANRORC-mechanism but by an EA and/or AE-mechanism. Treatment of 4,5-dibromo-2,6-diphenylpyrimidine with potassium amide under the above-mentioned conditions leads to a mixture of 4-amino-5-bromo-2,6-diphenylpyrimidine and 4-amino-2,6-diphenylpyrimidine. Evidence is presented that in the formation of 4-amino-5-bromo-2,6-diphenylpyrimidine the ANRORC-mechanism is operative to the extent of about 20 %. The synthesis of the 1(3)-"N-enriched 4-bromo-2,6-diphenyl-and the 4,5-dibromo-2,6-diphenyl-pyrimidine is described.
Part V on the ANRORC mechanism. Previous paper in this series: J. de Valk and H . C. van der Plas, Rec. Trav. Chim. Pays-Bas 92, 145 (1973). Part XXXI on pyrimidines from this laboratory. See for part XXX R. A. F. Deeleman and H . C. van der Plas, idem 92, 317 (1973). J. de Valk and H . C. v a n der Plas, ibid. 90, 1239 (1971). ANRORC mechanism. Part V 92 (1973) RECUEIL 443 See also, J. de Valk and H. C. van der Plus, Rec. Trav. Chim. Pays-Bas 91, 1414 (1972). * R. M. Anker and A. H. Cook, J. Chem. SOC. 1941, 323.
By treatment with potassium amide in liquid ammonia at -7S0, 4-chloro-5-cyano-6-phenylpyrimidine is converted into 4-amino-5-cyano-6-phenylpyrimidine; l-amino-2,2-dicyano-l-phenylethene is formed as a minor reaction product. Evidence is presented, using the labelled compounds 4-chloro-5-cyano-
6-phenyl-[1(3)-'5N]-and 4-chlor0-5-['~C]cyano-6-phenylpyrimidine that ithe conversion into the corresponding 4-amino compound proceeds completely according to the ANRORC mechanism, ii the I4C-cyano function remains nearly completely extranuclear. The synthesis of the I5N-and ''C-labelled 4-chloro-S-cyano-6-phenylpyrimidines is described.
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