Marcelis, A. T. M.; Van der Plas, H. C. published an article on January 10 ,1986. The article was titled 《Ring transformations of heterocycles with nucleophiles. 33. Cycloadditions of 5-nitropyrimidines with ynamines. Formation of 3-nitropyridines, N-5-pyrimidyl-α-carbamoylnitrones, and 2,2a-dihydroazeto[2,3-d]-3,5-diazocines》, and you may find the article in Journal of Organic Chemistry.Formula: C6H7N3O4 The information in the text is summarized as follows:
The reaction of pyrimidines containing an electron-withdrawing substituent at C-5 with ynamines RCCR1 (I; R,R1 = Me, Et2N; Ph, Me2N; Ph, pyrrolidino) was studied. 5-(Ethoxycarbonyl)- and 5-(methylsulfonyl)pyridine undergo [4 + 2] cycloaddition to yield the substituted pyridines II and III resp. 5-Nitropyrimidines containing 2- and/or 4(6)-alkoxy or Me groups give a variety of products upon reaction with I. 4,6-Dimethoxy-5-nitropyrimidine undergoes [4 + 2] cycloaddition to give pyridine derivative IV (R2 = MeO) upon reaction with I (R = Me, R1 = Et2N) (V). Nitrone VI (R2 = MeO) is formed as main product upon reaction of V with 2,4-dimethoxy-5-nitropyrimidine. 5-Nitropyrimidines unsubstituted at C-4 and C-6 give dihydroazeto[2,3-d]diazocines upon reaction with 2 equiv of V. 4-Methoxy-5-nitropyrimidine yields pyridine IV and nitrone VI (R3 = H, R4 = MeO) upon reaction with V, and from 4-methyl-5-nitropyriidine, the pyridines IV (R2 = H, Me) dihydroazetodiazocine VII, and a nitrone are formed. Ynamine I (R = Ph; R1 = Me2N) is less reactive than V and does not react to form dihydroazetodiazocines with the 5-nitropyrimidines. Instead, nitrone VIII (R5 = H) and pyridine IX are formed upon reaction of I (R = Ph, R1 = Me2N) with 5-nitropyrimidine, and nitrone VIII (R5 = Ph) is formed with 2-phenyl-5-nitropyrimidine. In the experiment, the researchers used 2,4-Dimethoxy-5-nitropyrimidine(cas: 30561-07-0Formula: C6H7N3O4)
2,4-Dimethoxy-5-nitropyrimidine(cas: 30561-07-0) is a member of ether. When aromatic ethers are exposed to halogen in the presence or absence of a catalyst, they undergo halogenation, such as bromination.Formula: C6H7N3O4
Referemce:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia