4-Chloro-7-tosyl-7H-pyrrolo[2,3-d]pyrimidine
[CAS# 479633-63-1]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyrimidine compound
• Name: 4-Chloro-7-tosyl-7H-pyrrolo[2,3-d]pyrimidine
• Synonyms: 4-Chloro-7-(4-methylphenylsulfonyl)-7H-pyrrolo[2,3-d]pyrimidine
• Molecular Formula: C₁₃H₁₀ClN₃O₂S
• Molecular Weight: 307.76
• CAS Registry Number: 479633-63-1
• EC Number: 811-000-2
• SMILES: CC1=CC=C(C=C1)S(=O)(=O)N2C=CC3=C2N=CN=C3Cl

Properties

• Density: 1.49

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H315-H319
• Safety Statements: P264-P264+P265-P280-P302+P352-P305+P351+P338-P321-P332+P317-P337+P317-P362+P364

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Eye irritation	Eye Irrit.	2	H319
Skin irritation	Skin Irrit.	2	H315

Discovery and Applications

The discovery of 4-chloro-7-tosyl-7H-pyrrolo[2,3-d]pyrimidine stems from the development of novel pyrrolopyrimidine derivatives with enhanced biological properties. The researchers aimed to combine the structural features of pyrrolopyrimidine, a scaffold known for its pharmacological potential, with the reactivity of chlorine and tosyl groups. The synthesis of the compound involves a multistep process involving cyclization of appropriate precursors and subsequent chlorination and mesylation steps. The typical approach involves starting from a pyrimidine derivative, introducing the chlorine substituent via electrophilic aromatic substitution, and attaching the mesylate group using mesyl chloride.

4-Chloro-7-mesyl-7H-pyrrolo[2,3-d]pyrimidine is a key intermediate in the synthesis of drugs, particularly those targeting kinases. Kinase inhibitors are an important class of drugs used in cancer therapy, as they can selectively inhibit enzymes involved in cellular signaling pathways that are critical for cancer cell growth and survival. The structural features of this compound allow it to participate in the formation of kinase inhibitors as a core building block, allowing the introduction of various functional groups to generate compounds with specific inhibitory activities.

Furthermore, the tosyl group of this compound can serve as a protecting or leaving group, facilitating further modifications of complex synthetic pathways. This makes 4-chloro-7-tosyl-7H-pyrrolo[2,3-d]pyrimidine a versatile tool in medicinal chemistry for the development of a variety of therapeutic agents, including anticancer drugs and other bioactive molecules.

In organic synthesis, 4-chloro-7-tosyl-7H-pyrrolo[2,3-d]pyrimidine is valued for its reactivity, which can be used to build more complex molecules. The presence of the chloro group allows for nucleophilic substitution reactions, while the tosyl group provides control over a variety of transformations, including deprotection or coupling reactions. This versatility makes it a useful intermediate for the synthesis of heterocyclic compounds, which are important in medicinal chemistry and materials science.

The ability of this compound to serve as a key intermediate in the construction of a variety of chemical entities highlights its role in the development of new methods for the synthesis of complex organic molecules. Its inclusion in multistep synthetic schemes expands the toolkit of synthetic chemists for the creation of new compounds.

Ongoing research focuses on optimizing its synthesis and exploring its potential in developing new drugs and materials. Research aims to improve the efficiency of its synthetic routes, increase yields and shorten reaction times. In addition, research on its applications will continue to discover new possibilities in creating advanced materials and therapeutic agents, driving innovation in academic and industrial fields.

References

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