23951-85-1Relevant academic research and scientific papers
Microwave-assisted simple synthesis of 2-anilinopyrimidines by the reaction of 2-chloro-4,6-dimethylpyrimidine with aniline derivatives
Angelini, Guido,Campestre, Cristina,Gasbarri, Carla,Kóti, János,Keglevich, Gy?rgy,Scotti, Luca
, p. 12249 - 12254 (2020/04/20)
A series of 2-anilinopyrimidines including novel derivatives has been obtained from 2-chloro-4,6-dimethylpyrimidine by aromatic nucleophilic substitution with differently substituted anilines under microwave conditions. The substituents had a significant impact on the course and efficiency of the reaction. The results reported herein demonstrate the efficacy of microwaves in the synthesis of the title heterocyclic compounds as compared to the results obtained with conventional heating. The 2-anilinopyrimidines described are of potential bioactivity.
One-pot two-step solvent-free rapid and clean synthesis of 2-(substituted amino)pyrimidines by microwave irradiation
Goswami, Shyamaprosad,Hazra, Anita,Jana, Subrata
experimental part, p. 1175 - 1181 (2009/12/25)
abs A series of diversely 2-(substituted amino)pyrimidines (along with ring substitution) has been synthesized under solvent- and catalyst-free microwave conditions from substituted guanidines and β-diketones. The substituted guanidines are synthesized from (S)-methylisothiourea sulfate and different amines (various alkyl, aryl, or heterocyclic and also chiral amines) under microwave irradiation. These two-step reactions are performed in one-pot without isolating any intermediate. This protocol has been successfully applied for the synthesis of bisaminopyrimidines and 2-substituted aminopyrimidines containing chiral moiety where chirality remains undisturbed.
A novel hydride-mediated reductive rearrangement of amide: a facile synthesis of pyrimidyl and triazinyl amines
Chen, Xiang,Wu, Jun,Shang, Zhicai,Chen, Meifeng,Sun, Yanping,Lv, Jing,Lei, Meikang,Zhang, Peizhi
, p. 495 - 499 (2008/04/13)
LiAlH4 and NaBH4 were found to mediate the conversion of 2-(pyrimidyl-2-ylsulfanyl)-N-arylbenzamides and 2-(triazinyl-2-ylsulfanyl)-N-arylbenzamides into pyrimidyl and triazinyl amines under notably mild conditions via a novel reductive rearrangement mechanism. These reactions invent a new route to prepare amines, which are a kind of important biologically active compounds and provide the first insight into a novel hydride-promoted reductive rearrangement of amides.
Dimroth-Type Ring Transformation of 1,4,6-Trisubstituted-2(1H)-Pyrimidinethiones with Ammonia and Primary Alkyl Amines
Kashima, Choji,Katoh, Akira,Yokota, Yuko,Omote, Yoshimori
, p. 1942 - 1946 (2007/10/02)
1,4,6-Trisubstituted-2(1H)-pyrimidinethiones (Ia-k) underwent Dimroth-type ring transformation with ammonia and prymary alkyl amines in the presence of silver perchlorate to afford 2-(N-substituted)aminopyrimidines (IIa, c, d, f, j, k) and pyrimidinium perchlorates (IIIa-c, e-j), respectively.Furthermore, pyrimidinium perchlorates (III) were converted into 2(1H)-pyrimidinones (IV) in high yields by hydrolysis with concentrated hydrochloric acid.Keywords --- Dimroth-type ring transformation reaction; ammonia; primary alkyl amines; 2-(N-substituted)aminopyrimidines; silver perchlorate; 2-(N-substituted)aminopyrimidinium perchlorates; hydrolysis; concentrated hydrochloric acid
