29274-24-6

Basic information

• Product Name: 5-Chloropyrazolo[1,5-a]pyrimidine
• Synonyms: 5-CHLOROPYRAZOLO[1,5-A]PYRIMIDINE;5-Chloropyrazolo[1,5-a]py...;Pyrazolo[1,5-a]pyriMidine, 5-chloro-;5-chloro-4,5-dihydropyrazolo[1,5-a]pyrimidine
• CAS NO: 29274-24-6
• Molecular Formula: C₆H₄ClN₃
• Molecular Weight: 153.57
• Product Categories: Heterocycle-Pyrimidine series
• Mol File: 29274-24-6.mol
• Article Data: 18

Chemical Properties

• Appearance: /
• Density: 1.514 g/cm³
• Refractive Index: 1.713
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: -0.49±0.30(Predicted)
• CAS DataBase Reference: 5-Chloropyrazolo[1,5-a]pyrimidine(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Chloropyrazolo[1,5-a]pyrimidine(29274-24-6)
• EPA Substance Registry System: 5-Chloropyrazolo[1,5-a]pyrimidine(29274-24-6)

Safety Data

• RIDADR: UN2811
• HazardClass: IRRITANT
• Hazardous Substances Data: 29274-24-6(Hazardous Substances Data)

Usage

Uses

5-Chloropyrazolo[1,5-a]pyrimidine was used in the preparation of β-substituted biarylphenylalanine amides as selective amino amide dipeptidyl peptidase IV inhibitors for treatment of type 2 diabetes.

InChI:InChI=1/C6H4ClN3/c7-5-2-4-10-6(9-5)1-3-8-10/h1-4H

Upstream product

• 1159981-95-9 5-bromopyrazolo[1,5-a]pyrimidine 
• 29274-22-4 4H,5H-pyrazolo[1,5-a]pyrimidine-5-one 
• 29274-22-4 pyrazolo[1,5-a]pyrimidine-5-ol 

Downstream Products

• 705262-65-3 5-iodo-pyrazolo[1,5-a]pyrimidine 
• 1228351-86-7 3-pyrazolo[1,5-a]pyrimidin-5-ylethynyl-benzonitrile 
• 1364890-59-4 (R)-5-(4,4-difluoro-2-(3-fluorophenyl)pyrrolidin-1-yl)pyrazolo[1,5-a]pyrimidine 
• 1256162-95-4 5-(3-chlorophenylamino)pyrazolo[1,5-a]pyrimidine-3-carbaldehyde 
• 1256163-44-6 5-(4-isopropoxyphenylamino)pyrazolo[1,5-a]pyrimidine-3-carbaldehyde 
• 1256163-42-4 5-(3-(morpholinomethyl)phenylamino)pyrazolo[1,5-a]pyrimidine-3-carbaldehyde 
• 1256163-40-2 5-((5-(4-chlorophenylamino)pyrazolo[1,5-a]pyrimidin-3-yl)methylene)thiazolidine-2,4-dione 
• 1256163-39-9 5-(4-chlorophenylamino)pyrazolo[1,5-a]pyrimidine-3-carbaldehyde 
• 1256163-35-5 5-(2-fluorophenyl)pyrazolo[1,5-a]pyrimidine-3-carbaldehyde 
• 1256163-29-7 5-(4-(2-(dimethylamino)ethoxy)phenylamino)pyrazolo[1,5-a]pyrimidine-3-carbaldehyde 
• 1256163-25-3 5-(3-isopropoxyphenylamino)pyrazolo[1,5-a]pyrimidine-3-carbaldehyde 
• 1256163-23-1 5-(3-(2-morpholinoethoxy)phenylamino)pyrazolo[1,5-a]pyrimidine-3-carbaldehyde 
• 1256163-21-9 5-(3-(4-methylpiperazin-1-yl)phenylamino)pyrazolo[1,5-a]pyrimidine-3-carbaldehyde 
• 1256163-16-2 5-(3-((diethylamino)methyl)phenylamino)pyrazolo[1,5-a]pyrimidine-3-carbaldehyde 

Relevant articles and documents

Optimization of pyrazolo[1,5-a]pyrimidines lead to the identification of a highly selective casein kinase 2 inhibitor

Casein kinase 2 (CK2) is a constitutively expressed serine/threonine kinase that has a large diversity of cellular substrates. Thus, CK2 has been associated with a plethora of regulatory functions and dysregulation of CK2 has been linked to disease development in particular to cancer. The broad implications in disease pathology makes CK2 an attractive target. To date, the most advanced CK2 inhibitor is silmitasertib, which has been investigated in clinical trials for treatment of various cancers, albeit several off-targets for silmitasertib have been described. To ascertain the role of CK2 inhibition in cancer, other disease and normal physiology the development of a selective CK2 inhibitor would be highly desirable. In this study we explored the pyrazolo [1,5-a]pyrimidine hinge-binding moiety for the development of selective CK2 inhibitors. Optimization of this scaffold, which included macrocyclization, led to IC20 (31) a compound that displayed high in vitro potency for CK2 (KD = 12 nM) and exclusive selectivity for CK2. X-ray analysis revealed a canonical type-I binding mode for IC20 (31). However, the polar carboxylic acid moiety that is shared by many CK2 inhibitors including silmitasertib was required for potency but limits the cellular activity of IC20 (31) and the cellular IC50 dropped to the low micromolar range. In summary, IC20 (31) represents a highly selective and potent inhibitor of CK2, which can be used as a tool compound to study CK2 biology and potential new applications for the treatment of diseases.

Method for efficiently synthesizing 5-chloropyrazolo[1,5-a]pyrimidine

The invention discloses a method for efficiently synthesizing 5-chloropyrazolo[1,5-a]pyrimidine. The synthesis route comprises: carrying out a reaction on a compound A and a compound B to obtain a compound C, and carrying out a reaction on the compound C and phosphorus oxychloride to obtain a compound D, ie., 5-chloropyrazolo[1,5-a]pyrimidine, wherein the reaction formulas A, B, C and D are defined in the specification. According to the present invention, the method has characteristics of mild synthesis condition, low influence of post-treatment on environment, simple process, inexpensive andeasily-available raw material, simple operation and wide industrial application prospect and market value, and is suitable for industrial large-scale production.

Heterocyclic Compound

The present invention provide a compound having an orexin receptor antagonistic activity, which is expected to be useful as medicaments such as agents for the prophylaxis or treatment of sleep disorder, depression, anxiety disorder, panic disorder, schizophrenia, drug dependence, Alzheimer's disease and the like. The present invention relates to a compound represented by the formula (I): wherein each symbol is as defined in the specification, or a salt thereof.