4-Chloro-5-iodo-7H-pyrrol[2,3-d]pyrimidine
[CAS# 123148-78-7]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyrimidine compound >> Iodopyrimidine
• Name: 4-Chloro-5-iodo-7H-pyrrol[2,3-d]pyrimidine
• Synonyms: 6-Chloro-7-iodo-7-deazapurine
• Molecular Formula: C₆H₃ClIN₃
• Molecular Weight: 279.47
• CAS Registry Number: 123148-78-7
• EC Number: 626-377-7
• SMILES: C1=C(C2=C(N1)N=CN=C2Cl)I

Properties

• Melting point: 179-183 °C

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H315-H319-H335
• Safety Statements: P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P330-P332+P313-P337+P313-P362-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - single exposure	STOT SE	3	H335
Acute toxicity	Acute Tox.	4	H302
Eye irritation	Eye Irrit.	2	H319
Eye irritation	Eye Irrit.	2A	H319

Discovery and Applications

The synthesis and characterization of 4-chloro-5-iodo-7H-pyrrolo[2,3-d]pyrimidine marks a milestone in organic chemistry. This heterocyclic compound has a fused pyrrole and pyrimidine ring system with chlorine at the 4-position and iodine at the 5-position. The presence of chlorine and iodine substituents on the pyrrolo[2,3-d]pyrimidine backbone imparts its unique reactivity. These substituents promote nucleophilic substitution and cross-coupling reactions, making this compound valuable in organic synthesis. Its heterocyclic nature and halogenation pattern also enhance its potential as a pharmacophore for drug design and development.

4-chloro-5-iodo-7H-pyrrolo[2,3-d]pyrimidine has important applications in medicinal chemistry and drug discovery. The structural features of this compound make it a promising backbone for the development of novel drugs targeting various biological pathways. Researchers have exploited its structural versatility and pharmacological activity to explore its antiviral, antibacterial, or anticancer potential.

In addition to medicinal chemistry, 4-chloro-5-iodo-7H-pyrrolo[2,3-d]pyrimidine is used in a variety of industrial applications. It is a building block for the synthesis of agrochemicals, dyes, and advanced materials. Its robust chemical structure allows it to be modified and optimized to tailor properties such as solubility, stability, and bioactivity.

In materials science, 4-chloro-5-iodo-7H-pyrrolo[2,3-d]pyrimidine can be used to develop functional materials and polymers. It is capable of controlled polymerization and cross-linking reactions, which enhances its usefulness in the manufacture of electronic components, coatings, and specialty polymers with enhanced performance characteristics.

References

2012. Functionalization of pyrrolo[2,3-d]pyrimidine by palladium-catalyzed cross-coupling reactions (review). Chemistry of Heterocyclic Compounds.
DOI: 10.1007/s10593-012-0986-2

2017. Synthesis of 2,6-Substituted 7-(Het)aryl-7-deazapurine Nucleobases (2,4-Disubstituted 5-(Het)aryl-pyrrolo[2,3-d]pyrimidines). Synthesis.
DOI: 10.1055/s-0036-1588443

2019. Pd/PTABS: An Efficient Catalytic System for the Aminocarbonylation of a Sugar-Protected Nucleoside. Synthesis.
DOI: 10.1055/s-0039-1690190