1027511-41-6

Basic information

• Product Name: ETHYL 6-BROMOPYRAZOLO[1,5-A]PYRIMIDINE-3-CARBOXYLATE
• Synonyms: ETHYL 6-BROMOPYRAZOLO[1,5-A]PYRIMIDINE-3-CARBOXYLATE;6-Bromo-3-(ethoxycarbonyl)pyrazolo[1,5-a]pyrimidine;6-Bromopyrazolo[1,5-a]pyrimidine-3-carboxylic acid ethyl ester
• CAS NO: 1027511-41-6
• Molecular Formula: C₉H₈BrN₃O₂
• Molecular Weight: 270
• Mol File: 1027511-41-6.mol
• Article Data: 7

Chemical Properties

• Appearance: /
• Density: 1.72
• Storage Temp.: 2-8°C(protect from light)
• CAS DataBase Reference: ETHYL 6-BROMOPYRAZOLO[1,5-A]PYRIMIDINE-3-CARBOXYLATE(CAS DataBase Reference)
• NIST Chemistry Reference: ETHYL 6-BROMOPYRAZOLO[1,5-A]PYRIMIDINE-3-CARBOXYLATE(1027511-41-6)
• EPA Substance Registry System: ETHYL 6-BROMOPYRAZOLO[1,5-A]PYRIMIDINE-3-CARBOXYLATE(1027511-41-6)

Safety Data

• Hazardous Substances Data: 1027511-41-6(Hazardous Substances Data)

Usage

General Description

Ethyl 6-bromopyrazolo[1,5-a]pyrimidine-3-carboxylate is a type of organic compound that falls under the category of heterocyclic aromatic compounds. As its name suggests, it has a pyrazolo[1,5-a]pyrimidine structure, which is a fused two-ring system, and it incorporates bromine and ethyl groups. It has the molecular formula C9H8BrN3O2. This chemical is known for its applications in the field of chemistry, particularly in organic synthesis and in the production of a range of pharmaceuticals and biological agents. It is generally used as an intermediate compound in these processes. It must be handled with care due to its potential hazards.

Upstream product

• 2065-75-0 2-Bromo-malonaldehyde 
• 1260243-04-6 ethyl 5-amino-1H-pyrazole-4-carboxylate 
• 6994-25-8 3-amino-4-pyrazolecarboxylic acid ethyl ester 

Downstream Products

• 1065081-05-1 N-(2-amino-2-oxoethyl)-6-(2,5-dichlorobenzyl)pyrazolo[1,5-a]pyrimidine-3-carboxamide 

Relevant articles and documents

Base catalyzed microwave assisted synthesis, characterization of 6-bromo-pyrazolo-[1,5-a]-pyrimidine-3-ethyl-carboxylate & its biological evaluation as CDKs inhibitor

In this work, 5-amino-1H-pyrazole-4-ethyl-carboxylate is synthesized by treating ethyl cyanoacetate and hydrazine hydrate in presence of different nanometal-oxide catalysts under solvent free microwave conditions. The yield quantity of the synthesized compounds varies for specific catalysts. 6-Bromopyrazolo-[1,5-a]-pyrimidine-3-ethyl-carboxylate was synthesized by reaction of 5-amino-1H-pyrazole-4-ethyl-carboxylate with 2-bromo-malonaldehyde using different bases. The rate of reactions were found to be influenced on the strength of bases. The synthesized compounds were confirmed by FT-IR, 1H NMR and LC-MS spectra. The compound 6-bromo-pyrazolo[1,5-a]pyrimidine-3-ethyl-carboxylate was then tested for in vitro biological activity as CDKs inhibitor. It showed better IC50 values for CDK4 and CDK6 than roscovitine. Thus, the synthesized compound is a selective inhibitor or acceptor for abnormal cancer cell line (CDKs).

Development of Potent and Selective Pyrazolopyrimidine IRAK4 Inhibitors

A series of pyrazolopyrimidine inhibitors of IRAK4 were developed from a high-throughput screen (HTS). Modification of an HTS hit led to a series of bicyclic heterocycles with improved potency and kinase selectivity but lacking sufficient solubility to progress in vivo. Structure-based drug design, informed by cocrystal structures with the protein and small-molecule crystal structures, yielded a series of dihydrobenzofurans. This semisaturated bicycle provided superior druglike properties while maintaining excellent potency and selectivity. Improved physicochemical properties allowed for progression into in vivo experiments, where lead molecules exhibited low clearance and showed target-based inhibition of IRAK4 signaling in an inflammation-mediated PK/PD mouse model.

CYCLIC ETHER DERIVATIVES OF PYRAZOLO[1,5-A]PYRIMIDINE-3-CARBOXYAMIDE

The invention relates to Spirocyclic ether derivatives of pyrazolo[1,5-a]pyrimidine-3-carboxyamide of general formula (I) which are inhibitors of phosphodiesterase 2, useful in treating central nervous system diseases and other diseases. In addition, the invention relates to processes for preparing pharmaceutical compositions as well as processes for manufacture the compounds according to the invention.