2802-62-2 | 4,6-DIFLUOROPYRIMIDINE

CAS:2802-62-2 | 4,6-DIFLUOROPYRIMIDINE,Description

4,6-Difluoropyrimidine is a chemical compound that belongs to the class of organic compounds known as pyrimidines. Pyrimidines are aromatic heterocyclic compounds containing two nitrogen atoms at positions 1 and 3 of the six-membered ring. The presence of fluorine atoms at the 4 and 6 positions of the pyrimidine ring can significantly alter the chemical and physical properties of the molecule, making it a valuable intermediate in various chemical syntheses, including pharmaceuticals and agrochemicals.

Synthesis Analysis

The synthesis of 4,6-difluoropyrimidine derivatives can be achieved through various methods. One approach involves the reaction of 2-polyfluoroalkylchromones with ketimines, which yields 2,6-diaryl-4-polyfluoroalkylpyridines and -pyrimidines in moderate to low yields. Another method includes the synthesis of C-6 substituted fluoroalkenyl 2,4-dimethoxypyrimidine derivatives through lithiation and subsequent reaction with ethyl pentafluoropropionate. Additionally, the synthesis of 2-methylthio-4,6-difluoropyrimidine, an important intermediate for herbicides, has been reported using a four-step reaction from various starting materials, including sulfocarbamidediethyl malonate and potassium fluoride.

Molecular Structure Analysis

The molecular structure of 4,6-difluoropyrimidine derivatives has been characterized using various spectroscopic techniques. For instance, the structure of C-6 fluoroalkenyl 2,4-dimethoxypyrimidine derivatives has been confirmed by ^1H, ^13C, and ^19F NMR spectra, as well as IR spectra, and in some cases, by X-ray crystal structure analysis. These analyses provide detailed information about the arrangement of atoms within the molecule and the nature of the substituents attached to the pyrimidine ring.

Chemical Reactions Analysis

4,6-Difluoropyrimidine and its derivatives can undergo a range of chemical reactions. For example, the activation of the C-F bond of 2,4,6-trifluoropyrimidine with nickel-assisted catalysts can lead to the synthesis of new pyrimidine and pyrimidinone derivatives. The reactivity of the fluorine atoms in the pyrimidine ring is a key factor in facilitating such transformations, which can be exploited to create a variety of functionalized compounds.

Physical and Chemical Properties Analysis

The physical and chemical properties of 4,6-difluoropyrimidine derivatives are influenced by the presence of fluorine atoms and other substituents on the pyrimidine ring. For instance, derivatives with extended pi-backbones and push-pull strategies exhibit improved intra-molecular charge transfer properties, which are beneficial for applications in charge transfer materials. The optical properties of some derivatives, such as those containing spirobifluoren groups, show good blue light emissions and excellent thermal stabilities. The introduction of fluorine atoms can also affect the solubility, thermal stability, and dielectric properties of polyimide films derived from pyrimidine-containing monomers.

Scientific Research Applications

• Pharmaceutical Intermediate

  • 2-ethoxy-4,6-difluoropyrimidine is an important pyrimidine compound and a key intermediate for synthesizing triazolopyrimidine sulfonamide-type medicament diclosulam.
  • The preparation method involves using urea as a raw material, preparing the intermediate 2-ethoxy-4,6-dihydroxypyrimidine through a one-pot two-step method, and then reacting with trifluoromethanesulfonic anhydride to generate an intermediate with trifluoromethanesulfonyl.
  • The intermediate is then reacted with a fluorinating agent for fluorination to obtain 2-ethoxy-4,6-difluoropyrimidine.
  • This method has the advantages of simple operation, high yield, and mild reaction conditions.

• Chemical Research

  • 4,6-Difluoropyrimidine is often used as a building block in chemical research.
  • It is a type of pyrimidine, which is a class of organic compounds with a wide range of applications in biochemistry, medicine, and other fields.

Safety And Hazards

4,6-Difluoropyrimidine is classified as a flammable liquid and vapor. It is harmful if swallowed, causes skin irritation, serious eye damage, and may cause respiratory irritation. It is recommended to avoid dust formation, breathing mist, gas or vapors, and contact with skin and eyes.

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