Production Method 1

905587-44-2

905587-43-1

Reaction Conditions

1.1 Reagents: Sodium borohydride Solvents: Methanol ;  0 °C; 1 h, rt

Reference

Use of Immobilized Amine Transaminase from Vibrio fluvialis under Flow Conditions for the Synthesis of (S)-1-(5-Fluoropyrimidin-2-yl)-ethanamine

Semproli, Riccardo; Vaccaro, Gianmarco; Ferrandi, Erica E. ; Vanoni, Marta; Bavaro, Teodora ; et al, ChemCatChem, 2020, 12(5), 1359-1367

Production Method 2

905587-44-2

905587-43-1

Reaction Conditions

1.1 Reagents: Sodium borohydride Solvents: Diethyl ether ,  Methanol ;  0 °C; 30 min, 18 - 25 °C

Reference

Discovery of 5-Chloro-N2-[(1S)-1-(5-fluoropyrimidin-2-yl)ethyl]-N4-(5-methyl-1H-pyrazol-3-yl)pyrimidine-2,4-diamine (AZD1480) as a Novel Inhibitor of the Jak/Stat Pathway

Ioannidis, Stephanos; Lamb, Michelle L.; Wang, Tao; Almeida, Lynsie; Block, Michael H.; et al, Journal of Medicinal Chemistry, 2011, 54(1), 262-276

1-(5-Fluoropyrimidin-2-yl)ethanol Raw materials

• 1-(5-fluoropyrimidin-2-yl)ethan-1-one

1-(5-Fluoropyrimidin-2-yl)ethanol Preparation Products

• 1-(5-Fluoropyrimidin-2-yl)ethanol (905587-43-1)

• 1. An amino group functionalized metal–organic framework as a luminescent probe for highly selective sensing of Fe3+ ions?
  Zhonghua Xiang,Chuanqi Fang,Sanhua Leng,Dapeng Cao J. Mater. Chem. A, 2014,2, 7662-7665
• 2. An antioxidant self-healing hydrogel for 3D cell cultures?
  Lei Yang,Yuan Zeng,Haibo Wu,Chunwu Zhou,Lei Tao J. Mater. Chem. B, 2020,8, 1383-1388
• 3. An aqueous ammonia sensor based on an inkjet-printed polyaniline nanoparticle-modified electrode
  Karl Crowley,Eimer O'Malley,Aoife Morrin,Malcolm R. Smyth,Anthony J. Killard Analyst, 2008,133, 391-399
• 4. An approach towards the synthesis of novel fused nitrogen tricyclic heterocyclic scaffolds via GBB reaction?
  Sandip Gangadhar Balwe,Yeon Tae Jeong Org. Biomol. Chem., 2018,16, 1287-1296
• 5. An astrophysically-relevant mechanism for amino acid enantiomer enrichment
  Stephen P. Fletcher,Richard B. C. Jagt,Ben L. Feringa Chem. Commun., 2007, 2578-2580

Introduction to 1-(5-Fluoropyrimidin-2-yl)ethanol (CAS No. 905587-43-1) in Modern Pharmaceutical Research

1-(5-Fluoropyrimidin-2-yl)ethanol, identified by the chemical abstracts service number 905587-43-1, is a compound of significant interest in the field of pharmaceutical chemistry. This molecule, featuring a fluoropyrimidine core linked to a hydroxylated ethyl group, has garnered attention due to its structural features and potential biological activities. The presence of a fluorine atom at the 5-position of the pyrimidine ring is particularly noteworthy, as fluorine substitution is a common strategy in drug design to enhance metabolic stability, binding affinity, and overall pharmacological efficacy.

The hydroxyl group at the 1-position of the ethyl chain introduces a polar moiety, which can influence solubility and interactions with biological targets. This combination of structural elements makes 1-(5-fluoropyrimidin-2-yl)ethanol a versatile scaffold for further derivatization and exploration in medicinal chemistry. Recent studies have highlighted its potential role in the development of novel therapeutic agents, particularly in oncology and anti-inflammatory applications.

One of the most compelling aspects of 1-(5-fluoropyrimidin-2-yl)ethanol is its connection to fluoropyrimidine-based inhibitors. These inhibitors have shown promise in targeting enzymes and pathways involved in cancer progression. For instance, fluoropyrimidines are well-known for their incorporation into nucleoside analogs that disrupt DNA synthesis in tumor cells. The compound’s ability to serve as a precursor or intermediate in synthesizing such analogs positions it as a valuable asset in drug discovery pipelines.

Recent advancements in computational chemistry and molecular modeling have further illuminated the potential of 1-(5-fluoropyrimidin-2-yl)ethanol. Researchers are leveraging these tools to predict how modifications to its structure—such as altering the length or branching of the ethyl chain—could enhance its bioactivity. This approach aligns with the growing trend toward structure-based drug design, where detailed knowledge of molecular interactions guides the development of more effective therapeutics.

The pharmaceutical industry has long been intrigued by fluorinated heterocycles, and 1-(5-fluoropyrimidin-2-yl)ethanol exemplifies why. The fluorine atom’s ability to modulate electronic properties and hydrogen bonding interactions makes it an invaluable tool for fine-tuning pharmacokinetic profiles. Moreover, the hydroxyl group provides opportunities for further functionalization, allowing chemists to explore diverse chemical space.

In clinical research, derivatives of fluoropyrimidines have demonstrated efficacy in treating various diseases, including solid tumors and hematological malignancies. While 1-(5-fluoropyrimidin-2-yl)ethanol itself may not be directly administered to patients, its role as a building block for more complex molecules is crucial. The compound’s stability under various reaction conditions makes it an attractive candidate for large-scale synthesis and subsequent medicinal chemistry efforts.

The integration of machine learning and artificial intelligence into drug discovery has also accelerated interest in compounds like 1-(5-fluoropyrimidin-2-yl)ethanol. These technologies can rapidly screen vast libraries of molecules for potential bioactivity, identifying promising candidates like this one for further investigation. Such innovations are reshaping how pharmaceutical researchers approach compound development, emphasizing efficiency and precision.

From a synthetic perspective, 1-(5-fluoropyrimidin-2-yl)ethanol offers unique challenges and opportunities. The need to maintain regioselectivity during fluorination reactions underscores the importance of advanced synthetic methodologies. Techniques such as transition-metal-catalyzed cross-coupling reactions have enabled more efficient access to fluorinated pyrimidines, making compounds like this one more accessible than ever before.

The broader impact of fluorinated small molecules on therapeutic development cannot be overstated. These compounds often exhibit improved pharmacological properties compared to their non-fluorinated counterparts, leading to better patient outcomes. As research continues into 1-(5-fluoropyrimidin-2-yl)ethanol, scientists are uncovering new ways to harness its potential for improving human health.

In summary, 1-(5-fluoropyrimidin-2-yl)ethanol (CAS No. 905587-43-1) represents a fascinating intersection of structural complexity and biological promise. Its role as a key intermediate in pharmaceutical synthesis, coupled with its connection to cutting-edge research in oncology and anti-inflammatory therapy, ensures its continued relevance in modern drug discovery efforts. As scientific understanding evolves, so too will the applications and derivatives derived from this remarkable compound.

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