89967-04-4Relevant articles and documents
Construction of a Pyrimidine Framework through [3 + 2 + 1] Annulation of Amidines, Ketones, and N, N-Dimethylaminoethanol as One Carbon Donor
Qin, Zemin,Ma, Yongmin,Li, Fanzhu
, p. 13734 - 13743 (2021/10/12)
An efficient, facile, and eco-friendly synthesis of pyrimidine derivatives has been developed. It involves a [3 + 2 + 1] three-component annulation of amidines, ketones, and one carbon source. N,N-Dimethylaminoethanol is oxidized through C(sp3)-H activation to provide the carbon donor. One C-C and two C-N bonds are formed during the oxidative annulation process. The reaction shows good tolerance to many important functional groups in air, making this methodology a highly versatile alternative, and significant improvement to the existing methods for structuring a pyrimidine framework, especially 4-aliphatic pyrimidines.
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. XXXIII. Synthesis of Alkyl Pyrimidinyl Ketones by Means of Nitrosation of Alkylpyrimidines
Sakamoto, Takao,Sakasai, Takeji,Yoshizawa, Hiroshi,Tanji, Ken-Ichi,Nishimura, Sumiko,Yamanaka, Hiroshi
, p. 4554 - 4560 (2007/10/02)
The reaction of 4-alkylpyrimidines with propyl nitrite under acidic conditions followed by deoximation of the resulting ketoximes gave alkyl pyrimidinyl ketones in satisfactory yields.As compared with the direct oxidation of the alkylpyrimidines with sele
