1683-75-6 | Pyrimidine, 2-amino-4-chloro-5-fluoro- (7CI,8CI)

CAS:1683-75-6 | Pyrimidine, 2-amino-4-chloro-5-fluoro- (7CI,8CI),Description

2-Amino-4-chloro-5-fluoropyrimidine is a compound that belongs to the class of pyrimidines, which are heterocyclic aromatic organic compounds similar to pyridine and characterized by a ring structure composed of nitrogen and carbon atoms. This particular compound is substituted with chlorine and fluorine atoms at specific positions on the pyrimidine ring, which can significantly affect its chemical and physical properties, as well as its reactivity and potential applications in various fields, including medicinal chemistry and materials science.

Synthesis Analysis

The synthesis of related fluorinated pyrimidines has been achieved through the fluorination of 2-aminopyridines and pyridin-2(1H)-ones using Selectfluor in aqueous solution, which provides good to high yields and high regioselectivities. Additionally, a modified condensation method has been developed for the synthesis of 5-substituted 2-amino-4,6-dihydroxypyrimidines, which can be further converted into 2-amino-4,6-dichloropyrimidines using the Vilsmeier–Haack–Arnold reagent. These methods highlight the potential pathways for synthesizing compounds similar to 2-amino-4-chloro-5-fluoropyrimidine.

Molecular Structure Analysis

The molecular structure of 2-amino-4-chloro-5-fluoropyrimidine can be inferred from studies on similar compounds. For instance, the crystal structure of a related compound, 2-amino-4-chloro-5-(4-methylbenzyl)-6-methylpyrimidine, has been determined by single-crystal X-ray diffraction, revealing a monoclinic space group and the presence of disordered chlorine atom and methyl group. This suggests that the molecular structure of 2-amino-4-chloro-5-fluoropyrimidine may also exhibit interesting features in its crystalline form.

Chemical Reactions Analysis

The reactivity of chloro- and fluoro-substituted pyrimidines can be quite diverse. For example, the transformation of a 3-fluoro-substituted pyridine derivative into fluorinated zolimidine has been achieved, demonstrating the potential for further chemical transformations. Moreover, the unusual aromatic substitution observed in the synthesis of 2-amino-4,6-dichloro-5-nitropyrimidine, where a nitro group is replaced by chloride, indicates that the reactivity of such compounds can lead to unexpected products.

Physical and Chemical Properties Analysis

The physical and chemical properties of 2-amino-4-chloro-5-fluoropyrimidine can be extrapolated from related compounds. For instance, the inhibitory effects of 2-amino-4,6-dichloropyrimidines on immune-activated nitric oxide production have been studied, with one derivative showing higher activity than the most potent reference compound. This suggests that the substitution pattern on the pyrimidine ring can significantly influence biological activity. Additionally, the synthesis and properties of novel polyimides derived from related aminopyrimidines indicate that these compounds can exhibit excellent thermal stability and mechanical properties, which could be relevant for the development of new materials.

Scientific Research Applications

Application 1: Preparation of 5-fluoro-2-amino pyrimidines

• Summary of the Application : 2-Amino-4-chloro-5-fluoropyrimidine can be used as a starting material for the preparation of 5-fluoro-2-amino pyrimidines.
• Methods of Application : This involves reacting 2-Amino-4-chloro-5-fluoropyrimidine with various amines in the presence of K2CO3, via a C-N bond-forming reaction.
• Results or Outcomes : The outcome of this reaction is the formation of 5-fluoro-2-amino pyrimidines.

Application 2: Preparation of 2,4-disubstituted-5-fluoropyrimidine

• Summary of the Application : 2-Chloro-5-fluoropyrimidine is used to prepare 2,4-disubstituted-5-fluoropyrimidine.
• Results or Outcomes : The outcome of this process is the formation of 2,4-disubstituted-5-fluoropyrimidine, which is a biologically active molecule seen in anticancer agents like 5-fluorouracil.

Safety And Hazards

The compound is classified under GHS07 for safety. The hazard statements include H302-H315-H319-H332-H335, indicating that it is harmful if swallowed, causes skin irritation, causes serious eye irritation, harmful if inhaled, and may cause respiratory irritation. Precautionary measures include avoiding breathing dust/fume/gas/mist/vapors/spray, wearing protective gloves/clothing/eye protection/face protection, and washing hands and face thoroughly after handling.

Future Directions

While specific future directions for 2-Amino-4-chloro-5-fluoropyrimidine were not found, it is known that pyrimidines have a wide range of pharmacological effects and are the subject of ongoing research. The compound’s potential for synthesis of novel pyrimidine analogs possessing enhanced anti-inflammatory activities with minimum toxicity is a promising area of study.

Relevant Papers There are several peer-reviewed papers and technical documents related to 2-Amino-4-chloro-5-fluoropyrimidine available at Sigma-Aldrich. These documents provide more detailed information about the compound and its properties.

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