23000-43-3

Basic information

• Product Name: 4-CHLORO-1-METHYL-1H-PYRAZOLO[3,4-D]PYRIMIDINE
• Synonyms: BUTTPARK 75\18-20;AKOS BBS-00002108;4-CHLORO-1-METHYL-1H-PYRAZOLO[3,4-D]PYRIMIDINE;4-CHLORO-1-METHYLPYRAZOLO[3,4-D]PYRIMIDINE;4-Chloro-1-methyl-1H-pyrazol[3,4-d]pyrimidine;1-Methyl-4-chloro-1H-pyrazolo[3,4-d]pyrimidine
• CAS NO: 23000-43-3
• Molecular Formula: C₆H₅ClN₄
• Molecular Weight: 168.58
• Product Categories: Heterocycle-Pyrimidine series
• Mol File: 23000-43-3.mol
• Article Data: 8

Chemical Properties

• Melting Point: 102-104
• Boiling Point: 294.6 °C at 760 mmHg
• Flash Point: 132 °C
• Appearance: /
• Density: 1.59 g/cm³
• Vapor Pressure: 0.00282mmHg at 25°C
• Refractive Index: 1.743
• Storage Temp.: Inert atmosphere,Store in freezer, under -20°C
• PKA: 1.46±0.10(Predicted)
• CAS DataBase Reference: 4-CHLORO-1-METHYL-1H-PYRAZOLO[3,4-D]PYRIMIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-CHLORO-1-METHYL-1H-PYRAZOLO[3,4-D]PYRIMIDINE(23000-43-3)
• EPA Substance Registry System: 4-CHLORO-1-METHYL-1H-PYRAZOLO[3,4-D]PYRIMIDINE(23000-43-3)

Safety Data

• Hazardous Substances Data: 23000-43-3(Hazardous Substances Data)

Usage

General Description

4-CHLORO-1-METHYL-1H-PYRAZOLO[3,4-D]PYRIMIDINE is a chemical compound with the molecular formula C5H4ClN5. It is a pyrazolopyrimidine derivative that is commonly used in the pharmaceutical industry for the synthesis of various biologically active molecules. 4-CHLORO-1-METHYL-1H-PYRAZOLO[3,4-D]PYRIMIDINE has a chlorine atom and a methyl group attached to a pyrazolopyrimidine ring, giving it unique properties and biological activities. It is used in the development of potential drugs for the treatment of various diseases, including cancer, inflammation, and infectious diseases. Additionally, it can also be used as a building block in the synthesis of different chemical compounds with potential biological activities.

InChI:InChI=1/C6H5ClN4/c1-11-6-4(2-10-11)5(7)8-3-9-6/h2-3H,1H3

Upstream product

• 5399-92-8 4-chloro-1H-pyrazolo[3,4-d]pyrimidine 
• 74-88-4 methyl iodide 

Downstream Products

• 130235-73-3 4-(3-chlorobenzyloxy)-1-methyl-1H-pyrazolo<3.4-d>pyrimidine 
• 130235-72-2 4-(2-chlorobenzyloxy)-1-methyl-1H-pyrazolo<3.4-d>pyrimidine 
• 130235-62-0 (4-Fluoro-phenyl)-(1-methyl-1H-pyrazolo[3,4-d]pyrimidin-4-yl)-methanone 
• 59564-10-2 (4-chloro-phenyl)-(1-methyl-1H-pyrazolo[3,4-d]pyrimidin-4-yl)-methanone 
• 130235-75-5 4-(4-chlorophenyl)-1-methyl-1H-pyrazolo<3.4-d>pyrimidine 
• 130235-74-4 4-(4-chlorobenzyloxy)-1-methyl-1H-pyrazolo<3.4-d>pyrimidine 
• 130235-77-7 4-chloro-benzoic acid 1,2-bis-(4-chloro-phenyl)-2-oxo-ethyl ester 
• 130235-64-2 (2-Chloro-phenyl)-(1-methyl-1H-pyrazolo[3,4-d]pyrimidin-4-yl)-methanone 
• 130235-76-6 1,2-bis(2-chlorophenyl)-2-oxoethyl 2-chlorobenzoate 
• 59564-07-7 (1-methyl-1H-pyrazolo[3,4-d]pyrimidin-4-yl)-phenyl-methanone 
• 59564-09-9 (4-methoxy-phenyl)-(1-methyl-1H-pyrazolo[3,4-d]pyrimidin-4-yl)-methanone 
• 130235-70-0 (3,4-Dimethoxy-phenyl)-(1-methyl-1H-pyrazolo[3,4-d]pyrimidin-4-yl)-methanone 
• 130235-63-1 (4-Bromo-phenyl)-(1-methyl-1H-pyrazolo[3,4-d]pyrimidin-4-yl)-methanone 
• 59564-08-8 (3-methoxy-phenyl)-(1-methyl-1H-pyrazolo[3,4-d]pyrimidin-4-yl)-methanone 

Relevant articles and documents

Palladium-catalyzed regioselective direct C–H arylation of?pyrazolo[3,4-d]pyrimidines

Nitrogenous bicycles are an apparently endless field of organic and biological research. In this study, we disclose an efficient pathway to the synthesis of the pyrazolo[3,4-d]pyrimidine scaffold in three steps from allopurinol. This key intermediate was engaged in the first example of regioselective C–H arylation catalyzed by palladium to access a library of 3-substituted-1-methyl-4-phenyl-1H-pyrazolo[3,4-d]pyrimidines.

ECTONUCLEOTIDE PYROPHOSPHATASE-PHOSPHODIESTERASE 1 (ENPP-1) INHIBITORS AND USES THEREOF

Disclosed herein are methods and compounds of augmenting and enhancing the production of type I IFNs in vivo. In some embodiments, the compounds disclosed herein are ENPP-1 inhibitors, pharmaceutical compositions, and methods for the treatment of cancer or a viral infection.

Design, synthesis, biological evaluation and molecular modeling of novel 1H-pyrazolo[3,4-d]pyrimidine derivatives as BRAFV600E and VEGFR-2 dual inhibitors

Aiming to explore novel BRAFV600E and VEGFR-2 dual inhibitors, a series of 1H-pyrazolo[3,4-d]pyrimidine derivatives were designed, synthesized and biologically evaluated in this study. Most of the synthesized 1H-pyrazolo[3,4-d]pyrimidine compounds displayed moderate to high potent activity in both enzymatic and cellular proliferation assays. Among these compounds, 9e, 9g, 9m and 9u showed remarkably high inhibitory activities against both BRAFV600E and VEGFR-2 kinase comparable to positive control Sorafenib. Particularly, compound 9u also showed potent anti-proliferative activity against BRAFV600E-expressing A375 (IC50 = 1.74 μM) and H-29 (IC50 = 6.92 μM) as well as VEGFR-2-expressing HUVEC (IC50 = 5.89 μM), which was also comparable to Sorafenib. Furthermore, kinase selectivity profile showed that 9u had almost poor or no significant inhibitory activity against wild-type BRAF and 15 other tested protein kinases. Flow cytometric analysis showed that compound 9u mainly arrested the A375 and HUVEC cell lines in the G0/G1 stage with a concentration-dependent effect. In addition, the molecular docking and molecular dynamics simulations suggested that 9u adopted a similar binding pattern with Sorafenib at the ATP-binding sites of BRAFV600E and VEGFR-2. Taken together, these results indicated that compound 9u may serve as novel lead compound in research on more effective BRAFV600E and VEGFR-2 dual inhibitors.