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Description
TCI D4045 2,5-Dichloropyrimidine is a heterocyclic building block based on a pyrimidine core carrying two chlorine atoms at the 2- and 5-positions. The pyrimidine ring is one of the most important scaffolds in medicinal chemistry, since it is present in nucleotide bases as well as in a very large number of drug compounds, including the kinase inhibitor class. In the synthesis laboratory, dichloropyrimidine compounds serve as scaffolds that can be functionalised in a stepwise manner, allowing researchers to install two different substituents at predetermined positions in order to build libraries of pyrimidine derivatives in a directed and systematic way.
The key characteristic that makes this compound valuable is the sharp difference in reactivity between its two chlorine atoms. The chlorine at position 2 sits between two strongly electron-withdrawing ring nitrogen atoms, so that position is highly activated toward nucleophilic aromatic substitution and is readily displaced by amines, alkoxides, or thiolates under moderate heating. In contrast, the chlorine at position 5 is far less activated toward nucleophilic substitution, yet it remains a good partner for palladium-catalysed cross-coupling reactions. This complementary reactivity gives synthetic chemists reliable control over the order in which each position is elaborated.
In Indonesian laboratories, this building block is typically used in university research groups, pharmaceutical research units, and contract synthesis facilities working on heterocyclic chemistry and medicinal chemistry programmes. It suits work that requires a defined starting scaffold for preparing pyrimidine derivatives, whether for exploratory synthesis, methodology development, or the preparation of compound series for further evaluation. Because it is supplied as a catalogue reagent from TCI, it also fits teaching and postgraduate research settings where consistent, well-defined starting materials are needed.
Laboratory Applications
- Nucleophilic aromatic substitution at the 2-position: the chlorine flanked by two ring nitrogens is strongly activated and is displaced cleanly by amines, alkoxides, or thiolates under moderate heating.
- Palladium-catalysed cross-coupling at the 5-position: although less activated toward nucleophilic attack, this chlorine remains a suitable partner for palladium-catalysed carbon–carbon and carbon–heteroatom bond formation.
- Sequential двух-step functionalisation of the pyrimidine core: the reactivity difference between the two chlorines allows two different substituents to be installed at predetermined positions in a controlled order.
- Medicinal chemistry scaffold preparation: the pyrimidine ring appears in nucleotide bases and in many drug compounds, including kinase inhibitors, making this a relevant starting scaffold for such programmes.
- Compound library construction: the stepwise, position-defined functionalisation makes this building block well suited to building series of pyrimidine derivatives in a directed and systematic manner.
Specifications
- Brand: TCI
- Product code: D4045
- CAS number: 22536-67-0
- Chemical name: 2,5-Dichloropyrimidine
- Category: Chemistry > Building Blocks > Heterocyclic Building Blocks
- Pack sizes and physical form: as listed in the current TCI catalogue entry for this product code; store according to the manufacturer's instructions on the product label
Handling and Storage
Store the container tightly closed in a cool, dry, and well-ventilated area, away from heat, ignition sources, and incompatible materials, and follow the storage conditions stated on the manufacturer's label and Safety Data Sheet for this product. Keep the material in its original supplier container, or in a clean, chemically compatible and clearly labelled container if transferred. Handle in a fume hood using appropriate personal protective equipment, including safety goggles, gloves, and a laboratory coat. Avoid inhalation of dust or vapours and contact with skin and eyes, close the container promptly after weighing to limit moisture uptake, and dispose of residues and contaminated materials in accordance with applicable chemical waste procedures.
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