89966-96-1Relevant articles and documents
Reaction of 2-Dimethylaminomethylene-1,3-diones with Dinucleophiles. VIII. Synthesis of Ethyl and Methyl 2,4-Disubstituted 5-Pyrimidinecarboxylates
Schenone, Pietro,Sansebastiano, Laura,Mosti, Luisa
, p. 295 - 305 (2007/10/02)
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-pyrimidinecarboxylateswere 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.
Studies on Pyrimidine Derivatives. XXXII. Reaction of 4-Substituted 2,6-Dimethylpyrimidine 1-Oxides with Phosphoryl Chloride
Sakamoto, Takao,Yoshizawa, Hiroshi,Kaneda, Sohichi,Hama, Yoshiaki,Yamanaka, Hiroshi
, p. 4533 - 4538 (2007/10/02)
The reaction of 2,6-dimethyl-4-phenylpyrimidine 1-oxide with phosphoryl chloride gave 4-chloromethyl-2-methyl-6-phenylpyrimidine exclusively.In contrast, 2,6-dimethyl-4-methoxy-pyrimidine 1-oxide and 2,6-dimethyl-4-dimethylaminopyrimidine 1-oxide reacted with the same reagent to give the corresponding 2-chloromethylpyrimidines predominantly.Keywords - pyrimidine N-oxide; chloromethylpyrimidine; phosphoryl chloride; siteselective reaction; substituent effect
