6-bromo-5-iodo-7-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine | CAS 2894018-46-1

PRODUCT OVERVIEW

6-bromo-5-iodo-7-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine | CAS 2894018-46-1 is a highly functionalized heterocyclic intermediate designed for advanced research and synthetic applications in medicinal chemistry and pharmaceutical development. Its unique substitution pattern — featuring bromine, iodine, and methyl functionalities on a fused pyrrolo-pyrimidine scaffold — provides a versatile building block for chemical diversification and structure-activity relationship (SAR) explorations.

This compound is especially valuable when the introduction of multiple halogens at key positions is required to tune biological activity, electronic properties, or to serve as a point of further derivatization via cross-coupling reactions.

CHEMICAL IDENTIFICATION

• CHEMICAL NAME: 6-Bromo-5-Iodo-7-Methyl-7H-Pyrrolo[2,3-d]pyrimidin-4-amine

• CAS REGISTRY NUMBER: 2894018-46-1

• MOLECULAR FORMULA: C7H6BrIN4

• MOLECULAR WEIGHT: 352.96 g/mol

STRUCTURAL DESCRIPTION

This compound consists of a fused heterocyclic system where a pyrrole ring is annulated with a pyrimidine core. The substitution pattern — with bromine at the 6-position, iodine at the 5-position, and a methyl group at the 7-position — creates an electron-rich and sterically defined heterocycle. An amine group at the 4-position further enhances its reactivity for functionalization.

Key features of the structure include:

• Halogen handles (Br and I) for cross-coupling reactions (e.g., Suzuki, Stille, Buchwald–Hartwig, Sonogashira)

• A heteroaromatic scaffold common in kinase inhibitors and nucleoside analogues

• A primary amine moiety providing additional reactivity and hydrogen-bonding potential

CHEMICAL PROPERTIES & PHYSICAL CHARACTERISTICS

Exact physical properties (e.g., melting point, purity assay) will be supplied on the Certificate of Analysis (COA) for each lot.

APPLICATIONS & RESEARCH USE

6-bromo-5-iodo-7-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine | CAS 2894018-46-1  is principally used as an intermediate in the synthesis of complex heterocycles for drug discovery and medicinal chemistry research. Representative applications include:

• MEDICINAL CHEMISTRY

• Lead optimization: As a core scaffold for generating analogues in hit-to-lead and lead optimization programs.

• SAR studies: The presence of halogen atoms and an amine group provides multiple vectors for systematic structure modification and biological evaluation.

• Targeted libraries: Suitable for building screening collections targeting kinases, GPCRs, and other therapeutic targets where heterocyclic frameworks are advantageous.

• ADVANCED SYNTHETIC INTERMEDIATE

• Cross-coupling chemistry: The bromine and iodine substituents serve as reactive sites for palladium-catalyzed coupling reactions to install diverse aryl, vinyl, or alkynyl groups.

• Amine functionalization: The 4-amine group allows for acylation, alkylation, and formation of heterocyclic derivatives.

• CHEMICAL BIOLOGY & TOOL COMPOUNDS

• Probe development: This intermediate can be transformed into molecular probes, fluorescent tags, or bioconjugates for pathway interrogation.

• Isotope labeling: The scaffold supports radiolabeling or stable isotope incorporation for ADME/PK studies.

SYNTHETIC CONSIDERATIONS

The design of this intermediate reflects contemporary synthetic strategy:

• Regioselective halogenation to introduce bromine and iodine at distinct positions

• Controlled methylation to impact electronic distribution and steric profile

• Fused heterocycle formation leveraging pyrrolo[2,3-d]pyrimidine chemistry

These features position the compound as a reliable precursor in multi-step synthetic schemes, enabling access to structurally complex targets with high precision.

SAFETY & HANDLING

When handling 6-bromo-5-iodo-7-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine | CAS 2894018-46-1, observe the following laboratory safety practices:

• Use appropriate personal protective equipment (PPE): lab coat, nitrile gloves, eye protection.

• Handle in a well-ventilated area or fume hood to avoid inhalation of dust or vapors.

• Avoid contact with skin and eyes.

• In case of contact, rinse thoroughly with water and seek medical attention as necessary.

Refer to the Safety Data Sheet (SDS) for complete hazard information, first-aid measures, and recommended storage conditions. This compound should be treated as a research chemical and not intended for human or animal consumption.

STORAGE RECOMMENDATIONS

To maintain integrity and performance:

• Store in a cool, dry place away from incompatible materials.

• Keep the container tightly closed when not in use.

• Protect from moisture and excessive heat.

Proper storage prolongs shelf life and ensures reproducibility in downstream applications.

QUALITY ASSURANCE

ResolveMass Laboratories Inc. provides this compound with:

• Verified chemical identity via NMR, LC-MS, and/or HRMS

• Purity assessment using validated analytical methods

• Lot-specific Certificate of Analysis (COA)

Our quality standards support rigorous research demands and reproducible results across projects.