6-Chloro-1H-pyrazolo[3,4-d]pyrimidine

Base Information

• Chemical Name: 6-Chloro-1H-pyrazolo[3,4-d]pyrimidine
• CAS No.: 23002-51-9
• Molecular Formula: C5H3ClN4
• Molecular Weight: 154.559
• Hs Code.: 2933990090
• Mol file: 23002-51-9.mol

Synonyms:1H-Pyrazolo[3,4-d]pyrimidine, 6-chloro-;

Chemical Property of 6-Chloro-1H-pyrazolo[3,4-d]pyrimidine

Chemical Property:

• Refractive Index: 1.74
• Boiling Point: 287.9±23.0 °C(Predicted)
• PKA: 9.27±0.20(Predicted)
• PSA: 54.46000
• Density: 1.653 g/cm³
• LogP: 1.00630
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility.: DMSO (Slightly), Ethyl Acetate (Slightly)

Purity/Quality:

98%,99%, ^*data from raw suppliers

6-Chloro-1H-pyrazolo[3,4-d]pyrimidine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Pyrazolo[3,4-d]pyrimidines have a close structural resemblance to the substrates for the enzyme xanthine oxidase, hypoxanthine (6-hydroxypurine) and xanthine (2,6-dihydroxypurine). These compounds ar e capable of binding to the enzyme and strongly inhibit its activity. They have been studied for their role in the treatment and prophylaxis of hyperuricemia in human patients as well as potential an ti-tumor agents. Pyrazolo[3,4-d]pyrimidines have a close structural resemblance to the substrates for the enzyme xanthine oxidase, hypoxanthine (6-hydroxypurine) and xanthine (2,6-dihydroxypurine). These compounds are capable of binding to the enzyme and strongly inhibit its activity. They have been studied for their role in the treatment and prophylaxis of hyperuricemia in human patients as well as potential anti-tumor agents.

Technology Process of 6-Chloro-1H-pyrazolo[3,4-d]pyrimidine

There total 1 articles about 6-Chloro-1H-pyrazolo[3,4-d]pyrimidine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 82.0%

2,4-dichloro-5-pyrimidinecarboxaldehyde (871254-61-4) → 6-chloro-1H-pyrazolo[3,4-d]pyrimidine (23002-51-9)

Guidance literature:

With hydrazine; In tetrahydrofuran; at 20 ℃; for 0.5h;

Reference yield: 93.0%

3,4-dihydro-2H-pyran (110-87-2) + 6-chloro-1H-pyrazolo[3,4-d]pyrimidine (23002-51-9) → 6-chloro-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[3,4-d]pyrimidine (1614233-64-5)

Guidance literature:

With pyridinium p-toluenesulfonate; In dichloromethane; for 6h; Reflux;

Reference yield: 91.0%

6-chloro-1H-pyrazolo[3,4-d]pyrimidine (23002-51-9) → 6-chloro-3-iodo-1H-pyrazolo[3,4-d]pyrimidine

Guidance literature:

With N-iodo-succinimide; In N,N-dimethyl-formamide; at 120 ℃; for 1h; Microwave irradiation;

DOI:10.1021/acs.jmedchem.7b01605

upstream raw materials:

2,4-dichloro-5-pyrimidinecarboxaldehyde

Downstream raw materials:

6-chloro-1-phenyl-1H-pyrazolo[3,4-d]pyrimidine

N-(1-methyl-1H-pyrazol-4-yl)-1H-pyrazolo[3,4-d]pyrimidin-6-amine

6-chloro-1-(2-nitrobenzyl)-1H-pyrazolo[3,4-d]pyrimidine

2-((6-chloro-1H-pyrazolo[3,4-d]pyrimidin-1-yl)methyl)aniline

Refernces

• 1、 Guan, Zhe,Huang, Lei,Ju, Qiurong,Li, Yin,Sun, Jinjin,Wang, Shuping,Wu, Shiqi,Xu, Yungen,Zhang, Lingzhi,Zhu, Qihua. "Discovery of novel dual extracellular regulated protein kinases (Erk) and phosphoinositide 3-kinase (pi3k) inhibitors as a promising strategy for cancer therapy". . . Retrieved 2021/06/14.
• 2、 -. "Indazole compound as FGFR kinase inhibitor and its preparation method and use". Paragraph 0427; 0428. . Retrieved 2016/10/08.