1246632-85-8 | Ethyl 2-Chloro-5-fluoropyrimidine-4-carboxylate

CAS:1246632-85-8 | Ethyl 2-Chloro-5-fluoropyrimidine-4-carboxylate,Description

Ethyl 2-chloro-5-fluoropyrimidine-4-carboxylate is a chemical compound with the molecular formula C7H6ClFN2O2. It is used as an intermediate in the synthesis of benzamide scaffolds, which are potent antagonists against P2X7 receptors.

Synthesis Analysis

The synthesis of Ethyl 2-chloro-5-fluoropyrimidine-4-carboxylate involves a reaction with potassium permanganate and sodium periodate in 1,4-dioxane and water at 25°C for 1 hour. The reaction mixture is then filtered, and the filtrate is diluted with ethyl acetate, aqueous sodium bicarbonate, and aqueous sodium chloride. The aqueous layer is extracted with ethyl acetate, and the combined organic layers are dried over sodium sulfate, filtered, and concentrated under reduced pressure. The resulting residue is purified by column chromatography to afford Ethyl 2-chloro-5-fluoropyrimidine-4-carboxylate.

Molecular Structure Analysis

The molecular weight of Ethyl 2-chloro-5-fluoropyrimidine-4-carboxylate is 204.59. The InChI code for this compound is 1S/C7H6ClFN2O2/c1-2-13-6(12)5-4(9)3-10-7(8)11-5/h3H,2H2,1H3.

Chemical Reactions Analysis

Ethyl 2-chloro-5-fluoropyrimidine-4-carboxylate can be used as a starting material for the preparation of 5-fluoro-2-amino pyrimidines by reacting with various amines in the presence of K2CO3, via C-N bond-forming reaction.

Physical And Chemical Properties Analysis

Ethyl 2-chloro-5-fluoropyrimidine-4-carboxylate is a liquid at room temperature. It should be stored in an inert atmosphere at 2-8°C.

Scientific Research Applications

Application in Cancer Treatment

• Specific Scientific Field : Cancer Biology
• Summary of the Application : Fluorinated pyrimidines (FPs) are used in the treatment of cancer. 5-Fluorouracil (5-FU) is the most widely used FP and is used to treat more than 2 million cancer patients each year.
• Methods of Application or Experimental Procedures : The methods for 5-FU synthesis include the incorporation of radioactive and stable isotopes to study 5-FU metabolism and biodistribution. RNA and DNA substituted with FPs are prepared for biophysical and mechanistic studies.
• Results or Outcomes : New insights into how FPs perturb nucleic acid structure and dynamics have resulted from both computational and experimental studies. Beyond the well-established role for inhibiting thymidylate synthase (TS) by the 5-FU metabolite 5-fluoro-2′-deoxyuridine-5′- O -monophosphate (FdUMP), recent studies have implicated new roles for RNA modifying enzymes that are inhibited by 5-FU substitution including tRNA methyltransferase 2 homolog A (TRMT2A) and pseudouridylate synthase in 5-FU cytotoxicity. Furthermore, enzymes not previously implicated in FP activity, including DNA topoisomerase 1 (Top1), were established as mediating FP anti-tumor activity.

Preparation of 5-fluoro-2-amino pyrimidines

• Specific Scientific Field : Organic Chemistry
• Summary of the Application : 2-Chloro-5-fluoropyrimidine, a compound similar to Ethyl 2-chloro-5-fluoropyrimidine-4-carboxylate, can be used as a starting material for the preparation of 5-fluoro-2-amino pyrimidines.
• Methods of Application or Experimental Procedures : This involves reacting 2-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.

Synthesis of Other Fluorinated Pyrimidines

• Specific Scientific Field : Organic Chemistry
• Summary of the Application : Ethyl 2-chloro-5-fluoropyrimidine-4-carboxylate could potentially be used as a starting material for the synthesis of other fluorinated pyrimidines.
• Methods of Application or Experimental Procedures : This would involve various organic reactions, such as nucleophilic substitution reactions with different nucleophiles, to replace the chlorine atom.
• Results or Outcomes : The outcome of this process would be the formation of new fluorinated pyrimidines, which could have various applications in medicinal chemistry and drug discovery.

Safety And Hazards

The compound is labeled with the GHS07 pictogram. The hazard statements associated with it are H302 (Harmful if swallowed), H315 (Causes skin irritation), H319 (Causes serious eye irritation), and H335 (May cause respiratory irritation). The precautionary statements are P261 (Avoid breathing dust/fume/gas/mist/vapors/spray), P280 (Wear protective gloves/protective clothing/eye protection/face protection), P301+P312 (IF SWALLOWED: Call a POISON CENTER or doctor/physician if you feel unwell), P302+P352 (IF ON SKIN: Wash with plenty of soap and water), and P305+P351+P338 (IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing).

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