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Description
2-Chloro-5-iodopyrimidine from TCI, catalogue code C3119, is a pyrimidine bearing two different halogen atoms at the two- and five-positions. Pyrimidine is one of the most important heterocyclic cores in biological and medicinal chemistry, since it forms the basic framework of the nucleic acid bases as well as of many active compounds. In synthetic laboratories this compound serves as a dihalogenated building block that allows researchers to install two different groups at separate positions of the same core in a sequential and controlled manner.
The added value of this compound lies in the striking difference in reactivity between its two halogens. The iodine atom at the five-position is an ideal partner for palladium-catalysed cross-coupling reactions, because the carbon–iodine bond undergoes oxidative addition most readily, so Suzuki, Sonogashira and Stille reactions can proceed under relatively mild conditions. The chlorine atom at the two-position, meanwhile, sits adjacent to two ring nitrogens that draw electron density away from it and make it strongly electrophilic, so it is ready to be displaced by amines or alkoxides through nucleophilic aromatic substitution. This difference is what gives high chemoselective control in synthetic route design.
In Indonesian laboratories this building block is typically used in university and institutional research groups working on organic synthesis, medicinal chemistry and heterocyclic chemistry. It suits work in which a pyrimidine core has to be elaborated step by step towards a target molecule, whether for the preparation of compound libraries, for structure–activity studies, or for teaching advanced synthesis at postgraduate level. It is handled with standard synthetic glassware, inert-atmosphere technique and routine chromatographic purification.
Laboratory Applications
Suzuki cross-coupling: the carbon–iodine bond at the five-position undergoes oxidative addition readily, so aryl and heteroaryl groups can be installed under relatively mild palladium-catalysed conditions.
Sonogashira coupling: the reactive iodine handle allows terminal alkynes to be attached selectively at the five-position, giving access to extended and rigid pyrimidine frameworks for further elaboration.
Stille coupling: organostannane partners can be joined at the iodinated position while the two-chloro group remains untouched, preserving it for a later, separate transformation step.
Nucleophilic aromatic substitution: the two-position chlorine is flanked by two ring nitrogens that make it strongly electrophilic and readily displaced by amines or alkoxides.
Sequential dual functionalisation in medicinal chemistry: the two halogens differ so markedly in reactivity that two different substituents can be installed in a controlled, chemoselective order.
Specifications
Brand: TCI
Catalogue code: C3119
CAS number: 32779-38-7
Category: Chemistry > Building Blocks > Heterocyclic Building Blocks
Pack sizes: available in the pack sizes listed for this catalogue item
Storage: keep in a cool, dry place in a tightly closed container, protected from light
Handling and Storage
Store the material in a cool, dry and well-ventilated place, in its original tightly closed container, protected from light and moisture and kept away from strong oxidising agents and sources of ignition. Amber glass bottles or the supplier's original packaging are suitable containers, and the cap should be closed firmly after each use to limit exposure to air and humidity. Handle the compound in a fume hood while wearing safety glasses, gloves and a laboratory coat, weigh it out carefully to avoid generating dust, and consult the manufacturer's safety data sheet before use and before disposal of any residues.
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