304693-64-9 | ETHYL 2-(TRIFLUOROMETHYL)PYRIMIDINE-5-CARBOXYLATE

CAS:304693-64-9 | ETHYL 2-(TRIFLUOROMETHYL)PYRIMIDINE-5-CARBOXYLATE,Description

Ethyl 2-(trifluoromethyl)pyrimidine-5-carboxylate is a chemical compound that belongs to the class of pyrimidine derivatives. Pyrimidines are heterocyclic aromatic organic compounds similar to benzene and pyridine, containing two nitrogen atoms at positions 1 and 3 of the six-member ring. The trifluoromethyl group attached to the pyrimidine ring at the second position and the ethyl ester at the fifth position are indicative of the compound's potential for various chemical reactions and biological activities.

Synthesis Analysis

The synthesis of related pyrimidine derivatives often involves multicomponent reactions, as seen in the preparation of ethyl 2-methylimidazo[1,2-a]pyrimidine-3-carboxylates, which are created by reacting ethyl 2-chloroacetoacetate with 2-aminopyrimidines. Similarly, ethyl 2-(dichloromethyl)-4-methyl-1-phenyl-6-thioxo-1,6-dihydropyrimidine-5-carboxylate is synthesized through a one-pot, three-component condensation involving ethyl 3-aminocrotonate, phenyl isothiocyanates, and 2,2-dichloroacetyl chloride. These methods suggest that the synthesis of ethyl 2-(trifluoromethyl)pyrimidine-5-carboxylate could also be achieved through a multicomponent reaction strategy, potentially involving a fluorinated building block to introduce the trifluoromethyl group.

Molecular Structure Analysis

The molecular structure of pyrimidine derivatives is often elucidated using X-ray diffraction crystallography, as demonstrated for compounds like ethyl 3-(4-chlorophenyl)-3,4-dihydro-6-methyl-4-oxo-2-(pyrrolidin-1-yl)furo[2,3-d]pyrimidine-5-carboxylate. Spectroscopic techniques such as FT-IR, 1H, and 13C NMR are also employed to characterize these molecules. Density functional theory (DFT) calculations can be used to predict the molecular geometry, vibrational frequencies, and NMR chemical shifts, which can then be compared with experimental data to confirm the structure.

Chemical Reactions Analysis

Pyrimidine derivatives are versatile in chemical reactions. For instance, ethyl 2-methylimidazo[1,2-a]pyrimidine-3-carboxylates can undergo alkaline hydrolysis to yield the corresponding carboxylic acids. The presence of the ethyl ester group in ethyl 2-(trifluoromethyl)pyrimidine-5-carboxylate suggests that it may also be susceptible to hydrolysis, among other reactions. The reactivity of the trifluoromethyl group could further lead to various substitutions and transformations, contributing to the compound's utility in medicinal chemistry and materials science.

Physical and Chemical Properties Analysis

The physical and chemical properties of pyrimidine derivatives, such as solubility, melting point, and reactivity, are influenced by their functional groups. The trifluoromethyl group is known for its electron-withdrawing properties, which can affect the acidity of adjacent hydrogen atoms and the overall stability of the molecule. The ethyl ester group could confer lipophilicity and influence the compound's solubility in organic solvents. The crystal structure and spectroscopic data provide insights into the compound's intermolecular interactions and potential for forming crystalline solids.

Safety And Hazards

The compound is classified under the GHS07 hazard class. It has hazard statements H302, H312, and H332, indicating that it is harmful if swallowed, in contact with skin, or if inhaled. Precautionary measures include avoiding breathing dust and contact with skin and eyes.

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