3-iodo-1H-pyrazolo[3,4-d]pyrimidin-4-amine | CAS 151266-23-8

PRODUCT OVERVIEW

3-iodo-1H-pyrazolo[3,4-d]pyrimidin-4-amine | CAS 151266-23-8 is a high-value heterocyclic research compound widely utilized as a synthetic intermediate in medicinal chemistry and drug discovery programs. The molecule belongs to the pyrazolo-pyrimidine class, a well-established scaffold in pharmaceutical research due to its structural similarity to purine systems and its strong relevance in kinase-targeted drug design.

This compound features a fused bicyclic heteroaromatic core, incorporating both pyrazole and pyrimidine rings, with a reactive iodine substituent at the 3-position and an amino functional group at the 4-position. This unique combination provides both synthetic flexibility and biological relevance, making it a preferred building block for advanced structure–activity relationship (SAR) studies.

ResolveMass Laboratories Inc. supplies this compound for research and development use, supporting pharmaceutical, biotechnology, and academic research initiatives that demand consistent quality and well-characterized intermediates.

CHEMICAL IDENTITY

• Chemical Name: 3-Iodo-1H-pyrazolo[3,4-d]pyrimidin-4-amine

• CAS Number: 151266-23-8

• Molecular Formula: C₅H₄IN₅

• Molecular Weight: 261.03 g/mol

• Chemical Class: Iodinated heterocyclic amine

• Structure Type: Fused pyrazolo-pyrimidine system

The presence of multiple ring nitrogens contributes to hydrogen-bonding capability and electronic tunability, both of which are essential for biological target engagement and downstream medicinal chemistry optimization.

PHYSICAL AND CHEMICAL PROPERTIES

3-iodo-1H-pyrazolo[3,4-d]pyrimidin-4-amine | CAS 151266-23-8 is typically observed as a white to pale yellow crystalline solid. Its aromatic and heterocyclic nature provides high thermal stability, with a melting point exceeding 300 °C, making it suitable for a wide range of synthetic conditions.

Key Characteristics Include:

• High aromatic stability

• Strong UV absorbance in the near-UV region

• Low volatility

• Limited solubility in water, with better solubility in polar aprotic organic solvents

The iodine atom significantly enhances the compound’s value as a synthetic handle, enabling regioselective cross-coupling reactions that expand molecular diversity efficiently.

SYNTHETIC VERSATILITY AND REACTIVITY

This compound is most commonly employed as a key intermediate rather than a final active pharmaceutical ingredient. The iodo substituent allows for a broad range of palladium-catalyzed transformations, including:

• Suzuki–Miyaura cross-coupling

• Sonogashira coupling

• Buchwald–Hartwig amination

• Other carbon–carbon and carbon–heteroatom bond-forming reactions

Meanwhile, the 4-amino group enables further derivatization through acylation, sulfonylation, or urea formation. Together, these functionalities make the molecule highly adaptable for the rapid synthesis of compound libraries during lead optimization.

The rigid fused ring system helps maintain conformational integrity, which is particularly beneficial when designing ligands for enzyme active sites.

APPLICATIONS IN DRUG DISCOVERY AND RESEARCH

Medicinal Chemistry

Pyrazolo[3,4-d]pyrimidine derivatives are widely recognized as ATP-competitive kinase inhibitors. As such, 3-iodo-1H-pyrazolo[3,4-d]pyrimidin-4-amine is frequently used in the synthesis of compounds targeting:

• Tyrosine kinases

• Serine/threonine kinases

• Cyclin-dependent kinases (CDKs)

• Receptor and non-receptor kinase families

The scaffold’s similarity to purine nucleobases allows it to effectively mimic ATP binding interactions, making it highly relevant in oncology, inflammatory disorders, and infectious disease research.

Anticancer and Antimalarial Research

Derivatives built from this intermediate have been explored in oncology programs, particularly where selective kinase inhibition is required. Additionally, the scaffold has demonstrated utility in research focused on parasitic kinases, supporting antimalarial drug discovery efforts.

Chemical Biology and Lead Optimization

Beyond direct therapeutic development, this compound is valuable in chemical biology studies, where kinase probes and pathway modulators are required. Its reactivity enables rapid analog generation, accelerating SAR exploration and hit-to-lead progression.

SAFETY AND HANDLING CONSIDERATIONS

This compound is intended for laboratory research use only and should be handled by trained professionals.

General Safety Considerations:

• May cause skin and eye irritation

• Avoid inhalation of dust

• Use appropriate personal protective equipment, including gloves and eye protection

• Handle in a well-ventilated laboratory or fume hood

Storage Recommendations:
Store in a tightly closed container under cool, dry conditions, protected from moisture and direct light to preserve chemical integrity over time.

QUALITY COMMITMENT FROM RESOLVEMASS LABORATORIES INC.

At ResolveMass Laboratories Inc., 3-iodo-1H-pyrazolo[3,4-d]pyrimidin-4-amine is supplied with a strong focus on analytical integrity, reproducibility, and research reliability. Each batch is produced and tested to meet stringent internal quality standards, ensuring suitability for demanding medicinal chemistry and discovery workflows.

Supporting documentation such as HPLC purity, NMR characterization, and mass spectrometry data is available to facilitate confident integration into regulated and non-regulated research environments.