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Reaction of 2‐dimethylaminomethylene‐1,3‐diones with dinucleophiles. VIII . Synthesis of ethyl and methyl 2,4‐disubstituted 5‐pyrimidinecarboxylates
Author(s) -
Sche Pietro,
Sansebastiano Laura,
Mosti Luisa
Publication year - 1990
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570270234
Subject(s) - chemistry , hydrolysis , benzamidine , guanidine , ethyl ester , derivative (finance) , alkaline hydrolysis , amidine , organic chemistry , reaction conditions , medicinal chemistry , enzyme , catalysis , financial economics , economics
Reaction of ethyl or methyl 2‐dimethylaminomethylene‐3‐oxoalkanoates with N‐C‐N dinucleophiles such as guanidine, acetamidine or benzamidine afforded in high yields the relative esters of 4‐substituted 2‐amino‐, 2‐methyl‐ or 2‐phenyl‐5‐pyrimidinecarboxylic acids, respectively. These esters were hydrolyzed to the corresponding carboxylic acids, which were converted by heating to 4‐substituted 2‐pyrimidinamines, 2‐methyl or 2‐phenylpyrimidines, respectively, generally in excellent yields. The 4‐unsubstituted ethyl 2‐amino‐, 2‐methyl‐ and 2‐phenyl‐5‐pyrimidinecarboxylates were obtained in moderate yields by reaction of the above dinucleophiles with ethyl 2,2‐diformylacetate. These esters were hydrolyzed and the corresponding acids (with the exception of the 2‐methyl derivative) were decarboxylated to give 2‐pyrimidinamine and 2‐phenylpyrimidine in satisfactory yields.