Ethyl 4-chloro-2-methylthio-5-pyrimidinecarboxylate
[CAS# 5909-24-0]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyrimidine compound >> Thiopyrimidine
• Name: Ethyl 4-chloro-2-methylthio-5-pyrimidinecarboxylate
• Molecular Formula: C₈H₉ClN₂O₂S
• Molecular Weight: 232.69
• CAS Registry Number: 5909-24-0
• EC Number: 227-619-0
• SMILES: CCOC(=O)C1=CN=C(N=C1Cl)SC

Properties

• Melting point: 60-63 °C

Safety Data

• Hazard Symbols: GHS05;GHS07 Danger
• Risk Statements: H315-H317-H318-H319-H335
• Safety Statements: P261-P264-P264+P265-P271-P272-P280-P302+P352-P304+P340-P305+P351+P338-P305+P354+P338-P317-P319-P321-P332+P317-P333+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - single exposure	STOT SE	3	H335
Eye irritation	Eye Irrit.	2	H319
Skin sensitization	Skin Sens.	1	H317
Serious eye damage	Eye Dam.	1	H318
Eye irritation	Eye Irrit.	2A	H319

Discovery and Applications

Ethyl 4-chloro-2-methylthio-5-pyrimidinecarboxylate is a specialized compound in the field of organic chemistry, known for its utility in various chemical syntheses and applications. This compound, with its unique pyrimidine-based structure and substituents, has garnered attention for its roles in both pharmaceuticals and agrochemicals.

The compound was first synthesized and characterized in the early 2000s as part of research focused on expanding the functional diversity of pyrimidine derivatives. Pyrimidines are six-membered aromatic heterocycles containing two nitrogen atoms, and their derivatives are crucial in the development of a wide range of bioactive compounds. The introduction of a chloro group, a methylthio group, and an ethyl ester functionality to the pyrimidine ring provides enhanced reactivity and versatility, making it a valuable intermediate in chemical synthesis.

The synthesis of ethyl 4-chloro-2-methylthio-5-pyrimidinecarboxylate typically involves multiple steps. The process starts with the preparation of a substituted pyrimidine derivative, followed by the introduction of the chloro and methylthio groups. The ethyl ester functionality is usually introduced through esterification reactions. This stepwise approach allows for precise control over the chemical properties of the final product.

In the pharmaceutical industry, ethyl 4-chloro-2-methylthio-5-pyrimidinecarboxylate is used as a building block for the synthesis of various bioactive molecules. The presence of the chloro and methylthio groups can influence the pharmacokinetics and pharmacodynamics of the final drug products. For instance, compounds derived from this pyrimidine derivative have been investigated for their potential as anti-inflammatory, anti-cancer, and antiviral agents. The structural modifications provided by the chloro and methylthio groups allow for the fine-tuning of biological activity and selectivity.

In agrochemicals, this compound serves as an intermediate for the development of herbicides and pesticides. The pyrimidine ring, combined with the chloro and methylthio substituents, contributes to the development of molecules with enhanced activity against specific pests and weeds. The ability to modify the electronic properties and steric effects of the compound through these substitutions is key to designing effective agrochemical agents.

Moreover, ethyl 4-chloro-2-methylthio-5-pyrimidinecarboxylate finds applications in materials science. The chemical reactivity of the pyrimidine ring and its substituents can be harnessed to develop novel materials with specific properties, such as improved stability or conductivity. This versatility extends the utility of the compound beyond traditional organic synthesis into advanced material applications.

In summary, ethyl 4-chloro-2-methylthio-5-pyrimidinecarboxylate is a valuable chemical substance with significant applications in pharmaceuticals, agrochemicals, and materials science. Its unique structure and functional groups provide a robust platform for the synthesis of diverse bioactive molecules and advanced materials, highlighting its importance in both research and industry.

References

2024. Design, synthesis, and antitumor activity evaluation of BF3-o, m, p-phenylenediamine bridged with pyrimidine-indole BF3 adduction derivatives. Molecular Diversity.
DOI: 10.1007/s11030-024-10863-3

2024. Design, Synthesis, and Biological Evaluation of a New Series of 2,4-Position Modified Pyrimidine Derivatives. Russian Journal of Bioorganic Chemistry, 50(2).
DOI: 10.1134/s1068162024020092

2023. An improved synthetic strategy for the multigram-scale synthesis of DNA-PK inhibitor AZD7648. Chemical Papers, 78(5).
DOI: 10.1007/s11696-024-03306-8