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Comprehensive Overview of 7-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine (CAS No. 7752-54-7): Properties, Applications, and Research Insights

7-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine (CAS No. 7752-54-7) is a heterocyclic organic compound belonging to the pyrrolopyrimidine family. This structurally unique molecule has garnered significant attention in pharmaceutical and biochemical research due to its potential as a kinase inhibitor scaffold and its role in modulating cellular signaling pathways. The compound's core structure features a fused pyrrole and pyrimidine ring system, with a methyl group at the 7-position and an amine at the 4-position, making it a valuable intermediate for drug discovery.

Recent studies highlight the growing interest in pyrrolopyrimidine derivatives like 7-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine for their applications in targeted cancer therapies. Researchers are particularly focused on its potential to inhibit tyrosine kinases, which are often overexpressed in tumors. This aligns with current trends in precision medicine, where users frequently search for terms like "small molecule inhibitors" or "anticancer drug candidates." The compound's ability to interfere with ATP-binding sites in kinases makes it a promising subject for structure-activity relationship (SAR) studies.

From a synthetic chemistry perspective, CAS No. 7752-54-7 serves as a versatile building block for medicinal chemistry optimization. Its amine functionality allows for straightforward derivatization, enabling the creation of libraries for high-throughput screening. This aspect resonates with industry professionals searching for "fragment-based drug design" or "scaffold hopping strategies." The methyl group at the 7-position enhances the compound's metabolic stability, addressing a common challenge in pharmacokinetic optimization—a hot topic in drug development forums.

The physicochemical properties of 7-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine contribute to its drug-likeness. With a molecular weight of 148.17 g/mol and moderate lipophilicity, it adheres to Lipinski's Rule of Five, a frequent search term among computational chemists. Its hydrogen bond donor/acceptor profile (2 donors, 3 acceptors) further supports its potential as a bioactive molecule. These characteristics explain why the compound appears in patents related to JAK/STAT pathway inhibitors—a trending topic in autoimmune disease research.

Beyond oncology, 7752-54-7 has shown relevance in neurodegenerative disease research, particularly in studies exploring kinase modulation in tauopathies. This connects with growing public interest in Alzheimer's disease therapeutics, as evidenced by search engine queries about "kinase targets in dementia." The compound's ability to cross the blood-brain barrier (predicted by in silico models) makes it particularly intriguing for CNS drug development.

Analytical characterization of 7-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine typically involves LC-MS (showing [M+H]+ at m/z 149.1) and NMR spectroscopy (with distinctive pyrrole proton signals at δ 6.5–7.5 ppm). These technical details cater to laboratory professionals searching for "pyrrolopyrimidine characterization methods." The compound's stability under physiological pH conditions (as per accelerated stability studies) further supports its utility in preclinical research.

In the context of green chemistry trends, synthetic routes to CAS No. 7752-54-7 have evolved to incorporate catalytic methods and atom-economical transformations. Recent publications describe improved yields via palladium-catalyzed cyclizations, addressing the demand for "sustainable heterocycle synthesis"—a rising search term among process chemists. These advancements align with the pharmaceutical industry's push toward environmentally benign manufacturing.

The commercial availability of 7-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine from specialty chemical suppliers has facilitated its adoption in academic and industrial labs worldwide. Quality control typically involves HPLC purity verification (>95%), with certificates of analysis detailing residual solvent levels—information highly sought after by purchasers comparing "pharma-grade pyrrolopyrimidines." Proper storage recommendations (2–8°C under inert atmosphere) ensure compound integrity for long-term research projects.

Looking forward, 7752-54-7 continues to inspire innovation in fragment-based lead discovery, particularly in allosteric kinase inhibitor design. Its presence in recent protein-ligand docking studies (with PDB IDs frequently mentioned in research papers) demonstrates ongoing relevance. As the scientific community increasingly searches for "privileged structures in drug design," this pyrrolopyrimidine core maintains its status as a valuable chemical tool for probing biological systems and developing next-generation therapeutics.

• 106105-23-1(7H-Pyrrolo[2,3-d]pyrimidin-4-amine, 7-phenyl-)
• 1824466-04-7(2-chloro-7-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine)
• 1500-85-2(7H-Pyrrolo[2,3-d]pyrimidin-4-amine)
• 14052-83-6(7H-Pyrrolo[2,3-d]pyrimidin-4-amine,7-ethyl-)
• 81965-19-7(1-methyl-1H-Pyrrolo[2,3-d]pyrimidin-4-amine)
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• 1444113-98-7(N-(3-cyanothiolan-3-yl)-2-[(2,2,2-trifluoroethyl)sulfanyl]pyridine-4-carboxamide)
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