Heterocyclic studies. Part XXXIX. Ring cleavage of some pyrimidine derivatives in alkali was written by Clark, Jim;Parvizi, Bahman;Colman, Robert. And the article was included in Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999) in 1976.Application In Synthesis of 4-Amino-6-chloropyrimidine-5-carbonitrile This article mentions the following:
4-(Substituted amino)-6-chloropyrimidines bearing a mesomeric electron-withdrawing substituent such as NO2, CN, CHO, or Ac at position 5 were cleaved by dilute NaOH at room temperature to give tetra-substituted alkenes. Thus I (0.01 mol. equivalent), H2O (20-30ml), and 2N NaOH (10ml), together with EtOH to aid partial dissolution, were stirred at ∼25° for 18-72 hr to give 98% H2NC(NHCH2Ph):C(CHO)CN. Unlike acid-catalyzed attacks on similar pyrimidines, the course of these basic reactions was not strongly influenced by steric interference between 4(6)- and 5-substituents. In the experiment, the researchers used many compounds, for example, 4-Amino-6-chloropyrimidine-5-carbonitrile (cas: 60025-09-4Application In Synthesis of 4-Amino-6-chloropyrimidine-5-carbonitrile).
4-Amino-6-chloropyrimidine-5-carbonitrile (cas: 60025-09-4) belongs to nitriles. The R-C-N bond angle in and nitrile is 180° which give a nitrile functional group a linear shape. Both the carbon and the nitrogen are sp hydridized which leaves them both with two p orbitals which overlap to form the two π bond in the triple bond. Some nitriles are manufactured by heating carboxylic acids with ammonia in the presence of catalysts. This process is used to make nitriles from natural fats and oils, the products being used as softening agents in synthetic rubbers, plastics, and textiles and for making amines.Application In Synthesis of 4-Amino-6-chloropyrimidine-5-carbonitrile
Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts