23002-51-9

Basic information

• Product Name: 6-Chloro-1H-pyrazolo[3,4-d]pyrimidine
• Synonyms: 6-Chloro-1H-pyrazolo[3,4-d]pyrimidine;1H-Pyrazolo[3,4-d]pyriMidine, 6-chloro-;6-chloro-1(2)H-pyrazolo[3,4-d]pyrimidine;2-Chlor-purin;6-Chlor-1H-pyrazolopyrimidin;QC-1184
• CAS NO: 23002-51-9
• Molecular Formula: C₅H₃ClN₄
• Molecular Weight: 154.56
• Product Categories: Heterocycle-Pyrimidine series;SF180085
• Mol File: 23002-51-9.mol

Chemical Properties

• Boiling Point: 287.9±23.0 °C(Predicted)
• Appearance: /
• Density: 1.653 g/cm³
• Refractive Index: 1.74
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility: DMSO (Slightly), Ethyl Acetate (Slightly)
• PKA: 9.27±0.20(Predicted)
• Stability: Moisture Sensitive
• CAS DataBase Reference: 6-Chloro-1H-pyrazolo[3,4-d]pyrimidine(CAS DataBase Reference)
• NIST Chemistry Reference: 6-Chloro-1H-pyrazolo[3,4-d]pyrimidine(23002-51-9)
• EPA Substance Registry System: 6-Chloro-1H-pyrazolo[3,4-d]pyrimidine(23002-51-9)

Safety Data

• Hazardous Substances Data: 23002-51-9(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
6-Chloro-1H-pyrazolo[3,4-d]pyrimidine is used as a therapeutic agent for the treatment and prophylaxis of hyperuricemia in human patients. Its ability to inhibit the enzyme xanthine oxidase helps regulate uric acid levels in the body, providing relief from conditions like gout and preventing the formation of uric acid stones.
Used in Oncology Research:
6-Chloro-1H-pyrazolo[3,4-d]pyrimidine is also used as a potential anti-tumor agent in the field of oncology. Its structural similarity to the substrates of xanthine oxidase allows it to interfere with the enzyme's activity, which may have implications for cancer treatment and prevention. Further research is needed to fully understand its potential applications in this area.

InChI:InChI=1/C5H3ClN4/c6-5-7-1-3-2-8-10-4(3)9-5/h1-2H,(H,7,8,9,10)

Upstream product

• 871254-61-4 2,4-dichloro-5-pyrimidinecarboxaldehyde 

Downstream Products

• 1296307-88-4 6-chloro-1-phenyl-1H-pyrazolo[3,4-d]pyrimidine 
• 1296307-10-2 N-(1-methyl-1H-pyrazol-4-yl)-1H-pyrazolo[3,4-d]pyrimidin-6-amine 
• 1296307-90-8 6-chloro-1-(2-nitrobenzyl)-1H-pyrazolo[3,4-d]pyrimidine 
• 1296307-91-9 2-((6-chloro-1H-pyrazolo[3,4-d]pyrimidin-1-yl)methyl)aniline 
• 1296307-92-0 N-(2-((6-chloro-1H-pyrazolo[3,4-d]pyrimidin-1-yl)methyl)phenyl)methanesulfonamide 
• 1296307-89-5 N-(2-((6-((1-methyl-1H-pyrazol-4-yl)amino)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)methyl)phenyl)methanesulfonamide 
• 1296307-25-9 2-((6-(1-methyl-1H-pyrazol-4-ylamino)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)methyl)benzamide 
• 1296307-26-0 N-methyl-N-(4-(6-(1-methyl-1H-pyrazol-4-ylamino)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)phenyl)methanesulfonamide 
• 1296307-09-9 2-((6-(1-methyl-1H-pyrazol-4-ylamino)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)methyl) benzonitrile 
• 1346162-23-9 tert-butyl-3-((6-chloro-1H-pyrazolo[3,4-d]pyrimidin-1-yl)methyl)piperidine-1-carboxylate 
• 1346161-55-4 N-(1-(2,2-difluoroethyl)-1H-pyrazol-4-yl)-1-((1-(methylsulfonyl)piperidin-3-yl)methyl)-1H-pyrazolo[3,4-d]pyrimidin-6-amine 
• 1346162-22-8 N-(1-(2,2-difluoroethyl)-1H-pyrazol-4-yl)-1H-pyrazolo[3,4-d]pyrimidin-6-amine 
• 287177-82-6 1H-pyrazolo[3,4-d]pyrimidin-6-amine 
• 1404437-70-2 6-chloro-1-(4-methoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidine 

Relevant articles and documents

Preparation method of 2, 4-dichloro-5-pyrimidinecarboxaldehyde and derivative thereof

The invention discloses a preparation method of 2, 4-dichloro-5-pyrimidinecarboxaldehyde and derivatives thereof. The method comprises the following steps:(1)by taking uracil as a raw material, addingDMF, slowly dropwise adding thionyl chloride at the temperature of 40 DEG C or below, controlling the temperature to be 35-40 DEG C after dropwise adding is finished, tracking by HPLC(High Performance Liquid Chromatography)until the raw material is completely reacted, cooling the system to room temperature, pouring into water, and separating out to generate 2, 4-dyhydroxyl-5-pyrimidinecarboxaldehyde; and(2)reacting the 2, 4-dihydroxy-5-pyrimidinecarboxaldehyde with phosphorus oxychloride to obtain 2, 4-dichloro-5-pyrimidinecarboxaldehyde; the method is good in operability and high in yield, and industrial production can be achieved.

Discovery of novel dual extracellular regulated protein kinases (Erk) and phosphoinositide 3-kinase (pi3k) inhibitors as a promising strategy for cancer therapy

Concomitant inhibition of MAPK and PI3K signaling pathways has been recognized as a promising strategy for cancer therapy, which effectively overcomes the drug resistance of MAPK signaling pathway-related inhibitors. Herein, we report the scaffold-hopping generation of a series of 1H-pyrazolo[3,4-d]pyrimidine dual ERK/PI3K inhibitors. Compound 32d was the most promising candidate, with potent inhibitory activities against both ERK2 and PI3Kα which displays superior anti-proliferative profiles against HCT116 and HEC1B cancer cells. Meanwhile, compound 32d possessed acceptable pharmacokinetic profiles and showed more efficacious anti-tumor activity than GDDC-0980 and the corresponding drug combination (BVD-523 + GDDC-0980) in HCT-116 xenograft model, with a tumor growth inhibitory rate of 51% without causing observable toxic effects. All the results indicated that 32d was a highly effective anticancer compound and provided a promising basis for further optimization towards dual ERK/PI3K inhibitors.

PYRAZOLO-PYRIMIDIN-AMINO-CYCLOALKYL COMPOUNDS AND THEIR THERAPEUTIC USES

Disclosed herein are pyrazolo-pyrimid in-ami no-cycloalkyl compounds, analogs thereof, pharmaceutical compositions comprising thereof and therapeutic uses therefor.

Indazole compound as FGFR kinase inhibitor and its preparation method and use

The invention provides an indazole compound as a FGFR kinase inhibitor and its preparation method and use and concretely provides a compound shown in the formula, wherein all groups are defined in the specification. The indazole compound has good FGFR kinase inhibition activity and can be used for preparation of a series of drugs for treating FGFR kinase activity-related diseases.

NOVEL PYRAZOLO[3,4-d]PYRIMIDINE COMPOUNDS

The present disclosure is directed to novel compounds of Formula (I), pharmaceutically acceptable salts, pro-drugs, biologically active metabolites, stereoisomers and isomers thereof wherein the variables are as defined herein. The compounds of Formula (I) are useful as kinase inhibitors and as such would be useful in treating certain conditions and diseases, especially inflammatory conditions and diseases and proliferative disorders and conditions, for example, rheumatoid arthritis, systemic lupus erythematosus, multiple sclerosis, Crohn's disease, psoriasis and asthma.

Pyrazolopyrimidines

Novel pyrazolopyrimidines of formula (I): are discussed. These pyrazolopyrimidines are capable of inhibiting the activity of cyclin-dependent kinases, most particularly cyclin-dependent kinase 1 (Cdk1), cyclin-dependent kinase 2 (Cdk2), and cyclin-dependent kinase 4 (Cdk4) and are thus useful, inter alia, in the treatment or control of cancer, in particular solid tumors. This invention also provides pharmaceutical compositions containing such compounds and to methods of treating or controlling cancer, most particularly the treatment or control of breast, lung, colon and prostate tumors.