Pyrimidine is an aromatic heterocyclic organic compound similar to pyridine. One of the three diazines (six-membered heterocyclics with two nitrogen atoms in the ring), it has the nitrogen atoms at positions 1 and 3 in the ring. 4595-59-9, formula is C4H3BrN2, Name is 5-Bromopyrimidine. 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. Synthetic Route of 4595-59-9.
Cook, Xinlan A. F.;Pantaine, Loic R. E.;Blakemore, David C.;Moses, Ian B.;Sach, Neal W.;Shavnya, Andre;Willis, Michael C. research published 《 Base-Activated Latent Heteroaromatic Sulfinates as Nucleophilic Coupling Partners in Palladium-Catalyzed Cross-Coupling Reactions》, the research content is summarized as follows. Heteroaromatic sulfinates, e.g., I, are effective nucleophilic reagents in Pd(0)-catalyzed cross-coupling reactions with aryl halides e.g., 4-methoxy-bromobenzene. However, metal sulfinate salts can be challenging to purify and solubilize in reaction media, and are not tolerant to multi-step transformations. Here base-activated, latent sulfinate reagents: β-nitrile and β-ester sulfones were introduced. It was shown that, under the cross-coupling conditions, these species generate the sulfinate salt in situ, which then undergo efficient palladium-catalyzed desulfinative cross-coupling with (hetero)aryl bromides to deliver a broad range of biaryls, e.g., II. These latent sulfinate reagents have proven to be stable through multi-step substrate elaboration, and amenable to scale-up.
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