The pyrimidine ring system has wide occurrence in nature as substituted and ring fused compounds and derivatives, 4595-59-9, formula is C4H3BrN2, Name is 5-Bromopyrimidine. including the nucleotides cytosine, thymine and uracil, thiamine (vitamin B1) and alloxan. Application of C4H3BrN2.
Wu, Zhi-Lei;Lan, Xingwang;Gao, Ning;Kang, Xiaomin;Wang, Zhenguang;Hu, Tianding;Zhao, Bin research published 《 Highly efficient hydroboration of alkynes catalyzed by porous copper-organic framework under mild conditions》, the research content is summarized as follows. Copper(I)-copper(II) pyrimidinecarboxylate metal-organic framework [(μ-5-PymCO2)4Cu2py2[Cu4I4]] (1; PymCO2H = 5-pyrimidinecarboxylic acid, py = pyridine) was prepared as active and robust catalyst for hydroboration of alkynes, yielding vinylboronates. The hydroboration of alkynes is crucial due to the wide applications in organic synthesis, while such reaction is often completed with low turnover frequency (TOF) value and long reaction time. Therefore, it is very important and necessary that the hydroboration of alkynes is performed with high TOF value, however the corresponding investigations have been never reported hitherto. Herein, a new Cu-organic framework 1 with mixed-valence Cu(I) and Cu(II) blocks was successfully synthesized and employed for the hydroboration of alkynes with bis(pinacolato)diboron (B2Pin2). The MOF 1 displays good thermostability and excellent solvent stability. Catalytic explorations reveal that 1 can serve as a high efficient heterogeneous catalyst for this reaction with a record TOF value of 310 h-1 under mild conditions, and 1 as catalysts which can be recycled at least five times without adding any cocatalysts. Mechanism investigations suggest that the Cu(I) and Cu(II) clusters in the framework of 1 have a synergistic catalytic effect in the hydroboration of alkynes, which can effectively activate the alkyne to react with B2Pin2. The d. functional theory (DFT) calculations explicitly elucidate the reaction pathways, and the results indicate that the Cu(I) and Cu(II) clusters in 1 as the catalytic sites can greatly reduce the Gibbs free energy of the hydroboration of alkyne in different degree, which accounts for the high catalytic activity of 1.
Application of C4H3BrN2, 5-Bromopyrimidine is a reactive intermediate that is used in the synthesis of 4-methoxyphenylboronic acid. 5-Bromopyrimidine has been shown to be nucleophilic, reacting with β-amino acids under basic conditions to form the corresponding 2-bromo amide. It also undergoes cross-coupling reactions with halides and can be used as a building block for other organic compounds. 5-Bromopyrimidine has optical properties that are characteristic of aromatic molecules, including strong absorption bands in the ultraviolet region and visible light region.
5-Bromopyrimidine undergoes direct metallation with lithuium diisopropylamide to yield 4-lithio-5-bromopyrimidine., 4595-59-9.
Referemce:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia