3-(3-fluoro-4-isopropoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine | CAS 1408087-64-8

PRODUCT SUMMARY

3-(3-fluoro-4-isopropoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine | CAS 1408087-64-8 is a structurally intricate heterocyclic compound featuring a fused pyrazolo[3,4-d]pyrimidine core linked to a substituted phenyl group. The phenyl ring is functionalized with a fluoro substituent and an isopropoxy moiety, while the heterocyclic nucleus bears an amino group at the 4-position. This unique combination of substituents imparts a blend of physicochemical properties that make the compound a versatile advanced intermediate in medicinal chemistry and related research domains.

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CHEMICAL IDENTIFICATION

• Common Name: 3-(3-fluoro-4-isopropoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine

• CAS Number: 1408087-64-8

• Molecular Formula: C₁₄H₁₄FN₅O

• Molecular Weight: 287.29 g/mol

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STRUCTURAL FEATURES & CHEMICAL CHARACTERISTICS

The compound integrates several significant structural motifs:

1. Pyrazolo[3,4-d]pyrimidine Core: A fused heterocycle combining pyrazole and pyrimidine rings — a scaffold frequently encountered in drug discovery due to its ability to mimic purine structures and engage in diverse molecular interactions with biological targets.

2. Substituted Phenyl Moiety: The phenyl ring is substituted with a fluorine atom (3-position) and an isopropoxy group (4-position).

   • The fluorine substituent contributes to increased lipophilicity, metabolic stability, and can influence binding affinity with protein targets.

   • The isopropoxy substituent can enhance overall molecular stability and impact solubility profiles.

3. Amino Functionality: Located at the heterocyclic 4-position, the –NH₂ group provides a site for hydrogen bonding and further chemical modification, which is valuable in synthesis and SAR (structure-activity relationship) studies.

Due to this architecture, CAS 1408087-64-8 exhibits characteristics suitable for synthetic manipulation, pharmacophore exploration, and advanced research utilization.

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APPLICATIONS IN RESEARCH & DEVELOPMENT

While detailed biological activity data specific to this exact compound may not be widely published, its structural classification places it firmly within a category of derivatives studied for biological and pharmacological relevance:

✔ Medicinal Chemistry & Drug Discovery
Pyrazolo[3,4-d]pyrimidine derivatives are widely employed as building blocks or key intermediates in the design and synthesis of bioactive molecules, especially in the development of kinase inhibitors, anti-inflammatory agents, and antineoplastic compounds. The core scaffold has been the subject of research toward selective modulation of enzyme targets and receptor systems due to its ability to mimic nucleotide structures and interact with active sites.

✔ Structure-Activity Relationship (SAR) Exploration
The presence of substituents such as fluorine and isopropoxy groups allows medicinal chemists to tune pharmacokinetic and physicochemical parameters systematically during lead optimization.

✔ Advanced Screening Libraries
Compounds like CAS 1408087-64-8 can be integrated into small-molecule libraries for high-throughput screening (HTS) to identify potential hits across diverse biological assays.

✔ Custom Synthesis Efforts
The accessible amine and substituted aromatic ring make it a valuable intermediate for further derivatization, including cross-coupling reactions, condensation chemistry, and heterocycle elaboration — techniques central to modern organic synthesis.

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REGULATORY & QUALITY ASSURANCE

Products supplied by ResolveMass Laboratories Inc. meet strict quality criteria indicated by purity specifications and analytical validation. CAS 1408087-64-8 is intended for RESEARCH USE ONLY and not for direct human consumption. Researchers should ensure compliance with their institutional, local, and national regulations when handling and disposing of chemical substances.

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CONCLUSION

3-(3-Fluoro-4-isopropoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine (CAS 1408087-64-8) is a strategically valuable heterocyclic intermediate for contemporary chemical research and drug discovery efforts. Its unique structure bridges targeted synthetic applications with potential translational outcomes in medicinal chemistry, making it a robust choice for integration into advanced workflows and compound libraries.