5-Bromo-4-chloro-7H-pyrrolo[2,3-d]pyrimidine
[CAS# 22276-95-5]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyrimidine compound >> Bromopyrimidine
• Name: 5-Bromo-4-chloro-7H-pyrrolo[2,3-d]pyrimidine
• Molecular Formula: C₆H₃BrClN₃
• Molecular Weight: 232.46
• CAS Registry Number: 22276-95-5
• EC Number: 622-419-3
• SMILES: C1=C(C2=C(N1)N=CN=C2Cl)Br

Properties

• Melting point: 221-225 °C

Safety Data

• Hazard Symbols: GHS06 Danger
• Risk Statements: H301
• Safety Statements: P264-P270-P301+P316-P321-P330-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	3	H301
Eye irritation	Eye Irrit.	2A	H319
Specific target organ toxicity - single exposure	STOT SE	3	H335
Skin irritation	Skin Irrit.	2	H315

Discovery and Applications

5-Bromo-4-chloro-7H-pyrrolo[2,3-d]pyrimidine is a versatile compound that is primarily used as a building block for the synthesis of pharmaceuticals and bioactive molecules. 5-Bromo-4-chloro-7H-pyrrolo[2,3-d]pyrimidine was first synthesized and characterized as part of an effort to develop novel heterocyclic compounds with potential bioactivity. The synthesis of this compound involves the functionalization of the pyrrolopyrimidine backbone, introducing bromine and chlorine atoms at specific positions. Typically, the process involves halogenation reactions using reagents such as bromine or chlorine sources under controlled conditions to achieve selective substitution on the pyrrolopyrimidine ring.

The chemical structure of 5-Bromo-4-chloro-7H-pyrrolo[2,3-d]pyrimidine consists of a pyrrolo[2,3-d]pyrimidine core with bromine at the 5-position and chlorine at the 4-position. This double halogenation imparts unique electronic and steric properties to the compound, making it a valuable intermediate in a variety of chemical reactions. Its halogenation position is key to its reactivity and ability to serve as a precursor for further functionalization in organic synthesis.

In medicinal chemistry, 5-bromo-4-chloro-7H-pyrrolo[2,3-d]pyrimidine is a key intermediate in the synthesis of pharmaceutical compounds. It is often used to develop kinase inhibitors, antiviral agents, and other bioactive molecules. The presence of bromine and chlorine allows for a variety of chemical modifications, enabling exploration of structure-activity relationships (SAR) and optimization of pharmacological properties.

Research involving 5-bromo-4-chloro-7H-pyrrolo[2,3-d]pyrimidine includes its use in high-throughput screening (HTS) for drug discovery. The compound is included in small molecule libraries tested against various biological targets, facilitating the identification of lead compounds with the desired activity profile. Its versatile structure supports the synthesis of analogs with different functional groups, aiding the development of novel therapeutics.

5-bromo-4-chloro-7H-pyrrolo[2,3-d]pyrimidine is also valuable in synthetic organic chemistry as a starting material for the creation of more complex molecules. Its halogenated positions can undergo cross-coupling reactions, such as Suzuki-Miyaura or Buchwald-Hartwig couplings, to introduce a variety of functional groups. This flexibility makes it a key component for the construction of heterocyclic skeletons and advanced intermediates for drug synthesis.

References

2016. Essential biphasic role for JAK3 catalytic activity in IL-2 receptor signaling. Nature Chemical Biology, 12(5).
DOI: 10.1038/nchembio.2056

2014. Chemistry of Fluorinated Indoles. Fluorine in Heterocyclic Chemistry Volume 1.
DOI: 10.1007/978-3-319-04346-3_3

2012. Functionalization of pyrrolo[2,3-d]pyrimidine by palladium-catalyzed cross-coupling reactions (review). Chemistry of Heterocyclic Compounds, 48(1).
DOI: 10.1007/s10593-012-0986-2