In the intricate world of organic synthesis, specific chemical intermediates stand out for their versatility and crucial role in creating complex molecular structures. 2,4-Dichloro-7H-pyrrolo[2,3-d]pyrimidine (CAS: 90213-66-4) is one such compound. Far beyond its well-known application as a Tofacitinib precursor, this heterocycle is a valuable tool for chemists engaged in a wide array of synthetic challenges. Understanding its reactivity and potential applications can unlock new pathways in drug discovery and material science.

Chemical Properties and Reactivity of 2,4-Dichloro-7H-pyrrolo[2,3-d]pyrimidine

The molecular structure of 2,4-Dichloro-7H-pyrrolo[2,3-d]pyrimidine, featuring a pyrrolo[2,3-d]pyrimidine fused ring system with two chlorine atoms at the 2 and 4 positions, dictates its chemical behavior. The chlorine atoms are labile and can be readily displaced through nucleophilic substitution reactions. This characteristic makes the compound an excellent starting material for introducing various functional groups onto the heterocyclic core. For instance, reactions with amines, alcohols, or thiols can lead to diverse substituted pyrrolo[2,3-d]pyrimidine derivatives, many of which possess significant biological activities.

Furthermore, the nitrogen atoms within the rings offer sites for alkylation or acylation, expanding the synthetic possibilities. Researchers often utilize Suzuki, Stille, or other cross-coupling reactions with appropriately functionalized derivatives to build more complex molecular architectures. The ability to selectively modify different positions on the ring system makes 2,4-Dichloro-7H-pyrrolo[2,3-d]pyrimidine a highly sought-after building block.

Applications Beyond Tofacitinib Synthesis

While its role in synthesizing Tofacitinib is prominent, the utility of 2,4-Dichloro-7H-pyrrolo[2,3-d]pyrimidine extends to other areas of pharmaceutical research and development. It serves as a scaffold for exploring novel kinase inhibitors, antiviral agents, and compounds targeting various cellular pathways. Medicinal chemists frequently purchase this intermediate to:

  • Synthesize libraries of related compounds for high-throughput screening.
  • Investigate structure-activity relationships (SAR) for new drug candidates.
  • Develop novel catalysts or ligands for organic transformations.
  • Create probes for biochemical assays.

For chemists and researchers looking to buy this versatile compound, sourcing from reputable suppliers is key. A reliable manufacturer will provide detailed specifications, including purity and physical properties, ensuring the success of complex synthetic endeavors. The availability of this intermediate at competitive prices from manufacturers in China further democratizes its access for global research efforts.