4-[2-(2-Amino-4,7-dihydro-4-oxo-1H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl]benzoic Acid Methyl Ester: A Comprehensive Introduction
4-[2-(2-Amino-4,7-dihydro-4-oxo-1H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl]benzoic Acid Methyl Ester, with the CAS number 155405-80-4, is a compound that has drawn significant attention in the chemical and pharmaceutical industries. This product is a crucial intermediate in various chemical syntheses and has potential applications in drug discovery. In this article, we will explore the properties, uses, applications in different fields, and preparation methods of this compound.
Properties of 4-[2-(2-Amino-4,7-dihydro-4-oxo-1H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl]benzoic Acid Methyl Ester
4-[2-(2-Amino-4,7-dihydro-4-oxo-1H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl]benzoic Acid Methyl Ester is a white to off – white crystalline powder. It has a specific molecular structure that gives it unique chemical and physical properties. The molecular formula of this compound is C16H16N4O3, and its molecular weight is approximately 312.32 g/mol. This compound is sparingly soluble in water but shows better solubility in organic solvents such as ethanol, methanol, and dimethyl sulfoxide (DMSO). Its melting point is in the range of [specific melting point range, if available], which is an important characteristic for its purification and handling in laboratory and industrial settings.
The chemical stability of 4-[2-(2-Amino-4,7-dihydro-4-oxo-1H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl]benzoic Acid Methyl Ester is relatively high under normal storage conditions. However, it may be sensitive to light, heat, and moisture. Therefore, it should be stored in a cool, dry place away from direct sunlight and sources of heat. In addition, it should be protected from air to prevent oxidation, especially in the presence of certain catalysts or reactive substances.
Uses of 4-[2-(2-Amino-4,7-dihydro-4-oxo-1H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl]benzoic Acid Methyl Ester
One of the primary uses of 4-[2-(2-Amino-4,7-dihydro-4-oxo-1H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl]benzoic Acid Methyl Ester is as an intermediate in the synthesis of more complex organic compounds. In the pharmaceutical industry, it can be used as a building block for the development of novel drugs. The pyrrolo[2,3 – d]pyrimidine core structure is a common motif in many biologically active molecules, and this compound provides a starting point for the introduction of various functional groups to modify the biological activity of the final product.
For example, it can be used in the synthesis of anti – cancer drugs. The amino and carbonyl groups in the molecule can participate in various chemical reactions, such as condensation, substitution, and addition reactions, to form new compounds with potential anti – tumor activity. By modifying the structure of 4-[2-(2-Amino-4,7-dihydro-4-oxo-1H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl]benzoic Acid Methyl Ester, researchers can design and synthesize drugs that target specific cancer – related pathways, such as inhibiting the growth of cancer cells or inducing apoptosis.
In addition to its application in anti – cancer drug development, this compound can also be used in the synthesis of anti – inflammatory drugs. The unique chemical structure of 4-[2-(2-Amino-4,7-dihydro-4-oxo-1H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl]benzoic Acid Methyl Ester allows it to interact with certain enzymes or receptors involved in the inflammatory response, thereby modulating the immune system and reducing inflammation.
Applications in Different Fields
Pharmaceutical Field
In the pharmaceutical field, 4-[2-(2-Amino-4,7-dihydro-4-oxo-1H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl]benzoic Acid Methyl Ester plays a vital role in drug discovery and development. As mentioned above, it can be used as a key intermediate in the synthesis of various drugs. Many pharmaceutical companies and research institutions are actively exploring its potential in the treatment of different diseases, including cancer, inflammation, and neurological disorders.
During the drug development process, this compound can be used in high – throughput screening assays to identify lead compounds with desired biological activities. By combining it with other chemical entities through various synthetic methods, a large number of analogs can be generated, and their biological activities can be evaluated. This approach helps to optimize the structure – activity relationship (SAR) of the compounds and improve the efficacy and safety of the final drugs.
Chemical Research Field
In the field of chemical research, 4-[2-(2-Amino-4,7-dihydro-4-oxo-1H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl]benzoic Acid Methyl Ester is used as a model compound for studying the reactivity and mechanism of certain chemical reactions. Its unique molecular structure contains multiple reactive sites, such as the amino group, carbonyl group, and aromatic ring, which can participate in a variety of reactions, including nucleophilic substitution, electrophilic addition, and cycloaddition reactions.
By studying the reactions of this compound, chemists can gain a deeper understanding of the reaction mechanisms and develop new synthetic methods. For example, the reaction of the amino group with different electrophiles can be used to introduce new functional groups, and the carbonyl group can participate in condensation reactions to form new heterocyclic compounds. These studies not only contribute to the development of organic chemistry but also provide theoretical support for the synthesis of more complex and functional molecules.
Preparation Methods of 4-[2-(2-Amino-4,7-dihydro-4-oxo-1H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl]benzoic Acid Methyl Ester
There are several methods for the preparation of 4-[2-(2-Amino-4,7-dihydro-4-oxo-1H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl]benzoic Acid Methyl Ester. One common method involves a multi – step synthesis starting from commercially available starting materials.
Step 1: Synthesis of the Pyrrolo[2,3 – d]pyrimidine Core
The first step is usually the synthesis of the pyrrolo[2,3 – d]pyrimidine core structure. This can be achieved by reacting appropriate pyrrole and pyrimidine derivatives under specific reaction conditions. For example, a pyrrole compound with a suitable leaving group can react with a pyrimidine compound containing an amino group in the presence of a base and a catalyst. The reaction may be carried out in an organic solvent such as dimethylformamide (DMF) or tetrahydrofuran (THF) at a certain temperature, usually ranging from room temperature to reflux temperature.
Step 2: Introduction of the Ethylbenzoic Acid Methyl Ester Group
After obtaining the pyrrolo[2,3 – d]pyrimidine core, the next step is to introduce the ethylbenzoic acid methyl ester group. This can be accomplished by a coupling reaction between the pyrrolo[2,3 – d]pyrimidine derivative and an appropriate ethylbenzoic acid methyl ester derivative. The coupling reaction may involve the use of a transition – metal catalyst, such as palladium or copper, and a suitable ligand. The reaction conditions, including the choice of solvent, temperature, and reaction time, need to be carefully optimized to achieve high yields and selectivity.
Step 3: Purification and Isolation
After the synthesis reaction is completed, the crude product needs to be purified and isolated. This can be done by various purification methods, such as column chromatography, recrystallization, or distillation. Column chromatography is a commonly used method, which can separate the desired product from impurities based on their different affinities for the stationary phase. Recrystallization is another effective method for purifying the product, which can improve the purity of the compound by dissolving it in a suitable solvent and then allowing it to crystallize out.
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