784150-41-0

Basic information

• Product Name: 6-BROMO-4-CHLORO-7H-PYRROLO[2,3-D]PYRIMIDINE
• Synonyms: 6-BROMO-4-CHLORO-7H-PYRROLO[2,3-D]PYRIMIDINE;6-BroMo-4-chloro-7H-pyrro...
• CAS NO: 784150-41-0
• Molecular Formula: C₆H₃BrClN₃
• Molecular Weight: 232.47
• Product Categories: CHIRAL CHEMICALS
• Mol File: 784150-41-0.mol

Chemical Properties

• Appearance: /
• Density: 1.996 g/cm³
• Refractive Index: 1.746
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• PKA: 9.52±0.50(Predicted)
• CAS DataBase Reference: 6-BROMO-4-CHLORO-7H-PYRROLO[2,3-D]PYRIMIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: 6-BROMO-4-CHLORO-7H-PYRROLO[2,3-D]PYRIMIDINE(784150-41-0)
• EPA Substance Registry System: 6-BROMO-4-CHLORO-7H-PYRROLO[2,3-D]PYRIMIDINE(784150-41-0)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 784150-41-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
6-Bromo-4-chloro-7H-pyrrolo[2,3-d]pyrimidine is utilized as a key intermediate in the synthesis of various pharmaceutical compounds. Its unique structure and functional groups make it a valuable component in the development of new drugs, particularly those targeting protein kinases, which play a crucial role in numerous cellular processes and are implicated in various diseases.
Used in Agrochemical Industry:
In the agrochemical sector, 6-Bromo-4-chloro-7H-pyrrolo[2,3-d]pyrimidine serves as a fundamental building block for the creation of novel agrochemicals. Its potential applications in this field include the development of new pesticides and herbicides, contributing to more effective and targeted agricultural solutions.
Used in Medicinal Chemistry Research:
6-Bromo-4-chloro-7H-pyrrolo[2,3-d]pyrimidine is employed as a research tool in medicinal chemistry, where it aids in the exploration of new chemical entities and the optimization of drug candidates. Its presence in various synthesized compounds allows researchers to study its effects on biological targets and understand its role in disease treatment and prevention.
Used in Drug Discovery:
As a potential therapeutic agent, 6-Bromo-4-chloro-7H-pyrrolo[2,3-d]pyrimidine is used in drug discovery for its potential applications in treating diseases such as cancer and infectious diseases. Its ability to modulate protein kinase activity makes it a promising candidate for the development of targeted therapies that can improve patient outcomes and address unmet medical needs.
Overall, 6-Bromo-4-chloro-7H-pyrrolo[2,3-d]pyrimidine is a significant chemical entity with diverse applications across various industries, particularly in the development of new pharmaceuticals and agrochemicals, as well as in research and drug discovery. Its unique properties and potential therapeutic applications make it a valuable asset in the field of medicinal chemistry.

InChI:InChI=1/C6H3BrClN3/c7-4-1-3-5(8)9-2-10-6(3)11-4/h1-2H,(H,9,10,11)

Upstream product

• 784150-40-9 6-bromo-4-chloro-7-(benzenesulfonyl)-7H-pyrrolo[2,3-d]pyrimidine 

Downstream Products

• 1351091-33-2 3-[(6-bromo-1H-pyrrolo[2,3-d]pyrimidin-4-yl)amino]-N-methylbenzenesulfonamide 
• 1351091-68-3 N-methyl-3-{[6-(4-pyridinyl)-1H-pyrrolo[2,3-d]pyrimidin-4-yl]amino}benzenesulfonamide 
• 1351091-57-0 N-methyl-3-({6-[3-(trifluoromethyl)phenyl]-1H-pyrrolo[2,3-d]pyrimidin-4-yl}amino)benzenesulfonamide 
• 1351091-71-8 N-methyl-3-{[6-(4-methylphenyl)-1H-pyrrolo[2,3-d]pyrimidin-4-yl]amino}benzenesulfonamide 
• 1351091-73-0 N-methyl-3-{[6-(3-methylphenyl)-1H-pyrrolo[2,3-d]pyrimidin-4-yl]amino}benzenesulfonamide 
• 1351091-54-7 N-methyl-3-{[6-(2-methylphenyl)-1H-pyrrolo[2,3-d]pyrimidin-4-yl]amino}benzenesulfonamide 
• 1351091-53-6 N-methyl-3-[(6-phenyl-1H-pyrrolo[2,3-d]pyrimidin-4-yl)amino]benzenesulfonamide 
• 1584150-82-2 6-({6-[(4-chlorophenyl)sulfonyl]-7H-pyrrolo[2,3-d]pyrimidin-4-yl}amino)-1,3-benzothiazol-2(3H)-one 
• 784150-43-2 C₁₂H₈BrN₃O₂ 
• 784150-42-1 6-bromo-4-chloro-7-methylpyrrolo[2,3-d]pyrimidine 

Relevant articles and documents

Identification of Purines and 7-Deazapurines as Potent and Selective Type i Inhibitors of Troponin I-Interacting Kinase (TNNI3K)

A series of cardiac troponin I-interacting kinase (TNNI3K) inhibitors arising from 3-((9H-purin-6-yl)amino)-N-methyl-benzenesulfonamide (1) is disclosed along with fundamental structure-function relationships that delineate the role of each element of 1 for TNNI3K recognition. An X-ray structure of 1 bound to TNNI3K confirmed its Type I binding mode and is used to rationalize the structure-activity relationship and employed to design potent, selective, and orally bioavailable TNNI3K inhibitors. Identification of the 7-deazapurine heterocycle as a superior template (vs purine) and its elaboration by introduction of C4-benzenesulfonamide and C7- and C8-7-deazapurine substituents produced compounds with substantial improvements in potency (>1000-fold), general kinase selectivity (10-fold improvement), and pharmacokinetic properties (>10-fold increase in poDNAUC). Optimal members of the series have properties suitable for use in in vitro and in vivo experiments aimed at elucidating the role of TNNI3K in cardiac biology and serve as leads for developing novel heart failure medicines.

Efficient formation of 4,6-disubstituted pyrrolo[2,3-d]pyrimidines: A novel route to TWS119, a glycogen synthase kinase-3β inhibitor

A concise synthesis of 4,6-disubstituted pyrrolo[2,3-d]pyrimidines is described. The key step involves the formation of an ether or thioether linkage along with concurrent ring closure in one-pot to yield the desired product in only two steps from a common intermediate. The reaction is chemoselective to incorporate phenol, thiophenol, and thiol. This method enabled efficient production of TWS119, a glycogen synthase kinase-3β inhibitor.

Heterocyclic Compounds Useful as RAF Kinase Inhibitors

The present invention provides compounds useful as inhibitors of Raf protein kinase. The present invention also provides compositions thereof, and methods of treating Raf-mediated diseases.