The pyrimidine ring system has wide occurrence in nature as substituted and ring fused compounds and derivatives, including the nucleotides cytosine, thymine and uracil, thiamine (vitamin B1) and alloxan. 4595-59-9, formula is C4H3BrN2, Name is 5-Bromopyrimidine. It is also found in many synthetic compounds such as barbiturates and the HIV drug, zidovudine. Synthetic Route of 4595-59-9.
Shcherbakov, Stanislav V.;Magometov, Artyom Yu;Vendin, Maksim V.;Shcherbakova, Viktoria Yu;Aksenov, Nicolai A.;Aksenov, Alexander V.;Naji, Osama;Rubin, Michael research published 《 Investigation of cationic transformations involving 5-ethynyl-4-arylpyrimidines》, the research content is summarized as follows. An innovative synthetic approach toward 5-R1CC-4-R2-substituted pyrimidines (R1 = Ph, 3,4-Me2C6H3, 2-naphthyl; R2 = 4-HOC6H4, 4-HO-3,5-Me2C6H2, 2-HO-5-EtC6H4, etc.) has been developed via acid-catalyzed electrophilic alkylation of phenols with 5-bromopyrimidine, followed by oxidation and palladium-catalyzed Sonogashira cross-coupling reaction. Reactions of these compounds in the presence of trifluoromethanesulfonic acid were investigated. It was discovered that these reactions take a different route for precursors with a different position of hydroxy group in an arene substituent.
Synthetic Route of 4595-59-9, 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