4-Chloropyrrolo[2,3-d]pyrimidine
[CAS# 3680-69-1]

Identification

• Classification: Biochemical >> Nucleoside drugs >> Nucleotides and their analogues
• Name: 4-Chloropyrrolo[2,3-d]pyrimidine
• Synonyms: 4-Chloro-1H-pyrrolo[2,3-d]pyrimidine; 6-Chloro-7-deazapurine
• Molecular Formula: C₆H₄ClN₃
• Molecular Weight: 153.57
• CAS Registry Number: 3680-69-1
• EC Number: 628-079-2
• SMILES: C1=CNC2=C1C(=NC=N2)Cl

Properties

• Solubility: 2.052e+004 mg/L (25 °C water)
• Density: 1.5±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.720, Calc.^*
• Melting point: 93.37 °C
• Boiling Point: 291.68 °C

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H315-H319-H335
• Safety Statements: P261-P264-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P362-P403+P233-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	3	H301
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2	H319
Chronic hazardous to the aquatic environment	Aquatic Chronic	3	H412
Specific target organ toxicity - single exposure	STOT SE	3	H335
Skin sensitization	Skin Sens.	1B	H317
Acute toxicity	Acute Tox.	4	H302
Eye irritation	Eye Irrit.	2A	H319

Discovery and Applications

4-Chloropyrrolo[2,3-d]pyrimidine is a heterocyclic compound with a fused pyrrole and pyrimidine ring system with a chlorine atom attached to the fourth position. This compound was originally synthesized as part of an effort to explore the chemical space of fused heterocyclic compounds for the development of potential drugs. The motivation for this discovery was to exploit the structural complexity and potential biological activity of heterocyclic compounds to develop new scaffolds for drug design.

4-Chloropyrrolo[2,3-d]pyrimidine is a key intermediate in drug synthesis. Its fused ring structure and active chlorine atom make it a versatile building block for the creation of a variety of bioactive molecules. It is particularly valuable in the development of kinase inhibitors, which are used in cancer therapy to block aberrant cell signaling pathways. The compound provides a scaffold for the introduction of various substituents that enhance binding affinity and specificity to target proteins.

The most important application of 4-chloropyrrolo[2,3-d]pyrimidine is the development of kinase inhibitors. Kinases are enzymes that play a key role in cell signaling and regulation, and their dysregulation is often associated with diseases such as cancer and inflammation. The compound's fused pyrrolopyrimidine structure enables it to effectively interact with the ATP binding site of kinases, thereby inhibiting their activity. This makes it a key component in the design of drugs that can treat various types of cancer by targeting specific kinases that are involved in tumor growth and proliferation.

In addition to cancer, 4-chloropyrrolo[2,3-d]pyrimidine is used as an anti-infective agent. Its unique structure enables it to combat bacterial and viral targets by interfering with essential biological processes. Derivatives that can be used to treat infections, especially those caused by drug-resistant pathogens, are currently being investigated, highlighting its importance in addressing the growing challenge of antimicrobial resistance.

In chemical biology, 4-chloropyrrolo[2,3-d]pyrimidine is used as a probe to study biological systems. Its ability to interact with proteins and nucleic acids makes it a valuable tool for studying cellular processes and molecular interactions. This application is essential for understanding disease mechanisms and identifying new therapeutic targets, providing insights into the basic biology of cells and tissues.

The compound is also used in synthetic chemistry as a building block for the creation of complex heterocyclic structures. Its reactivity allows the introduction of various functional groups, thereby synthesizing a variety of chemical entities. This versatility supports the development of new synthetic methods and the exploration of new chemical space, promoting the development of organic synthesis.

In materials science, the electronic and optical properties of 4-chloropyrrolo[2,3-d]pyrimidine derivatives have also been studied. These compounds can be used to develop organic semiconductors, light-emitting diodes (LEDs), and other advanced materials. The unique electronic structure of the fused pyrrolopyrimidine core provides potential applications for the design of electronic and photonic device materials with tailored properties.

References

2020. Pyrrolopyrimidines in Drug Discovery. Journal of Medicinal Chemistry, 63(15).
DOI: 10.1021/acs.jmedchem.0c00567