62802-38-4 | 5-BROMO-2-FLUOROPYRIMIDINE

CAS:62802-38-4 | 5-BROMO-2-FLUOROPYRIMIDINE,Description

Synthesis Analysis The synthesis of 5-Bromo-2-fluoropyrimidine involves palladium-catalysed cross-coupling reactions, showcasing its utility as an intermediate for the synthesis of various substituted pyrimidine compounds. An example of its application is demonstrated through the synthesis of novel 5-bromo-2-iodopyrimidine, further used in selective palladium-catalysed cross-coupling reactions with arylboronic acids and alkynylzincs to produce substituted pyrimidines efficiently (Goodby et al., 1996).

Molecular Structure Analysis The molecular structure of 5-Bromo-2-fluoropyrimidine and its derivatives is pivotal for their application in the synthesis of complex molecules. For instance, the preparation of 5-brominated and 5,5'-dibrominated 2,2'-bipyridines and 2,2'-bipyrimidines showcases the role of 5-Bromo-2-fluoropyrimidine derivatives in constructing metal-complexing molecular rods through Stille coupling and bromination processes (Schwab et al., 2002).

Chemical Reactions and Properties 5-Bromo-2-fluoropyrimidine undergoes various chemical reactions that highlight its versatility. The radiosynthesis of 2-amino-5-[18F]fluoropyridines from 5-Bromo-2-fluoropyrimidine illustrates its potential in radiofluorination and subsequent amination, yielding significant compounds for further applications (Pauton et al., 2019).

Physical Properties Analysis The synthesis and investigation of fluorinated 5-aryl-4-(hetero)aryl substituted pyrimidines from 5-Bromo-2-fluoropyrimidine reveal its critical role in producing compounds with promising antitubercular activity. This study sheds light on the physical properties of 5-Bromo-2-fluoropyrimidine derivatives and their biological efficacy (Verbitskiy et al., 2016).

Chemical Properties Analysis The chemical versatility of 5-Bromo-2-fluoropyrimidine is further demonstrated in its use as a halogen-rich intermediate for synthesizing pentasubstituted pyridines. The exploration of halogen dance reactions and electrophile trapping highlights the compound's unique chemical reactivity and its potential as a building block in medicinal chemistry (Wu et al., 2022).

Scientific Research Applications

• Medicinal Chemistry

  • 5-Bromo-2-fluoropyrimidine is a derivative of pyrimidine, a 6-membered heterocycle with two nitrogen heteroatoms. It’s used as a synthesis intermediate for active pharmaceutical ingredients (APIs).
  • It’s an essential building block for synthesising reldesemitiv , a fast skeletal muscle troponin activator for treatment of diseases that lead to diminished muscle function.

• Drug Discovery

  • 5-Bromo-2-fluoropyrimidine is a fluorinated pyrimidine building block used in drug discovery.
  • It can perform nucleophilic aromatic substitution on the fluoride group, Pd-catalysed carbon-carbon coupling on the bromide group and acid-catalysed vicarious nucleophilic substitution at the 4- and 6-positions.

• Organic Synthesis

  • This compound is used in organic synthesis due to its bromide and fluoride substituents at the para-position, enabling it for synthesising linear macromolecules under stepwise process.

• Semiconductors

  • 5-Bromo-2-fluoropyrimidine is also an ideal building block for semiconductors, due to its aromaticity and electron deficiency.
  • A host material of 5-(5-(2,4,6-triiso-propylphenyl)pyridin-2-yl)-5H-benzo[d]benzo-[4,5]imidazo[1,2-a]imidazole is synthesized from 5-bromo-2-fluoropyrimidine for OLED applications.

• Preparation of Push-Pull Molecules

  • 5-Bromo-2-fluoropyrimidine is used to prepare push-pull molecules, serving as an ‘electron-pulling’ moiety.
  • The bromide and fluoride substituents at the para-position enable it for synthesising linear macromolecules under a stepwise process.
  • It can perform nucleophilic aromatic substitution on the fluoride group, Pd-catalysed carbon-carbon coupling on the bromide group and acid-catalysed vicarious nucleophilic substitution at the 4- and 6-positions.

• Biochemical Reagent

  • 5-Bromo-2-fluoropyrimidine is a biochemical reagent that can be used as a biological material or organic compound for life science related research.

• Synthesis of Antituberculosis Agents

  • 5-Bromo-2-fluoropyrimidine has been used in the synthesis of novel 5-styryl-4-(hetero)aryl-pyrimidines.
  • These compounds have shown promising antituberculosis activity.
  • The synthesis involves a combination of the Pd-catalysed Suzuki cross-coupling and SNH reactions.

• Preparation of Farnesyltransferase Inhibitors

  • 5-Bromo-2-fluoropyrimidine has been used in the structure-based design and synthesis of potent, ethylenediamine-based, mammalian farnesyltransferase inhibitors.
  • These inhibitors have potential as anticancer agents.

Safety And Hazards

5-Bromo-2-fluoropyrimidine is considered hazardous by the 2012 OSHA Hazard Communication Standard (29 CFR 1910.1200). It can cause skin irritation, serious eye irritation, and may cause respiratory irritation. It is advised to avoid contact with skin and eyes, not to breathe dust, and not to ingest.

Future Directions

5-Bromo-2-fluoropyrimidine is used to prepare push-pull molecules, serving as an ‘electron-pulling’ moiety. It is also an essential building block for synthesising reldesemtiv, a fast skeletal muscle troponin activator for treatment of diseases that lead to diminished muscle function.

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