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

Base Information

• Chemical Name: 4-Chloro-1H-pyrazolo[3,4-d]pyrimidine
• CAS No.: 5399-92-8
• Molecular Formula: C5H3ClN4
• Molecular Weight: 154.559
• Hs Code.: 29335990
• European Community (EC) Number: 640-617-8
• NSC Number: 4937
• DSSTox Substance ID: DTXSID20277919
• Nikkaji Number: J2.444.875D
• Wikidata: Q72458260
• Mol file: 5399-92-8.mol

Synonyms:4-Chloro-1H-pyrazolo[3,4-d]pyrimidine;5399-92-8;4-Chloro-1H-pyrazolo(3,4-d)pyrimidine;4-Chloropyrazolo[3,4-d]pyrimidine;1H-Pyrazolo[3,4-d]pyrimidine, 4-chloro-;MFCD03030404;4-chloro-2H-pyrazolo[3,4-d]pyrimidine;NSC4937;4-chloro-1H-pyrazolo [3,4-d] pyrimidine;SCHEMBL11218;2,3,4 Trimethoxybenzaldehyde;DTXSID20277919;HMS1652C11;BCP26825;CS-D1776;NSC 4937;NSC-4937;BBL100167;STL227745;AKOS000266347;4-Chloro-1H-pyrazolo-3,4-dpyrimidine;AC-3600;MF-0708;PB20011;SDCCGMLS-0065537.P001;4-chloro-1H-pyrazolo[3,4-d]pyrmidine;4-chloro-5H-pyrazolo[3,4-d]pyrimidine;SY005568;4-Chloro-1H- pyrazolo[3,4-d]pyrimidine;A7847;BB 0257719;FT-0649592;EN300-27216;4-chloro-1H-pyrazolo[3 pound not4-d]pyrimidine;F0909-0060;Z1741971778;1821249-93-7

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

Chemical Property:

• Vapor Pressure: 7.5E-08mmHg at 25°C
• Melting Point: >350oC
• Refractive Index: 1.739
• Boiling Point: 348.315 °C at 760 mmHg
• PKA: 10.16±0.20(Predicted)
• Flash Point: 195.349 °C
• PSA: 54.46000
• Density: 1.653 g/cm³
• LogP: 1.00630
• Storage Temp.: Refrigerator
• Solubility.: DMSO (Slightly), Methanol (Slightly, Sonicated)
• XLogP3: 1.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 154.0046238
• Heavy Atom Count: 10
• Complexity: 131

Purity/Quality:

98% ^*data from raw suppliers

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

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=NNC2=C1C(=NC=N2)Cl
• Uses: Has a SK channel blocker effect. Has a SK channel blocker effect

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

There total 10 articles about 4-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: 83.0%

2,6-dichloro-pyrimidine carbaldehyde (5305-40-8) → 4-chloro-1H-pyrazolo[3,4-d]pyrimidine (5399-92-8)

Guidance literature:

With triethylamine; hydrazine; In 1,4-dioxane; at 20 ℃; for 1h;

Reference yield: 76.0%

4-hydroxypyrazolo(3,4-d)pyrimidine (315-30-0) → 4-chloro-1H-pyrazolo[3,4-d]pyrimidine (5399-92-8)

Guidance literature:

With N,N-dimethyl-formamide; trichlorophosphate; for 12h; Reflux;

DOI:10.1021/jm400233w

Reference yield: 74.0%

hydrazine hydrate (7803-57-8,79785-97-0) + 2,6-dichloro-pyrimidine carbaldehyde (5305-40-8) → 4-chloro-1H-pyrazolo[3,4-d]pyrimidine (5399-92-8)

Guidance literature:

2,6-dichloro-pyrimidine carbaldehyde; With triethylamine; In tetrahydrofuran; at 0 ℃; for 0.166667h; Inert atmosphere;

hydrazine hydrate; In tetrahydrofuran; at 0 - 20 ℃; for 1h; Inert atmosphere;

DOI:10.1055/s-0033-1338862

upstream raw materials:

Allopurinol

4-hydroxypyrazolo(3,4-d)pyrimidine

2,6-dichloro-pyrimidine carbaldehyde

hydrazine hydrochloride

Downstream raw materials:

4-chloro-1-(4-methoxybenzyl)-1H-pyrazolo[3,4-d]pyrimidine

4-chloro-2-cyclopentyl-2H-pyrazolo[3,4-d]pyrimidine

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

Refernces

• 1、 El Hafi, Mohamed,Naas, Mohammed,Loubidi, Mohammed,Jouha, Jabrane,Ramli, Youssef,Mague, Joel T.,Essassi, El Mokhtar,Guillaumet, Gérald. "Palladium-catalyzed regioselective direct C–H arylation of?pyrazolo[3,4-d]pyrimidines". . p. 927 - 933. Retrieved 2017/09/06.
• 2、 Fu, Yu,Wang, Yuanyuan,Wan, Shanhe,Li, Zhonghuang,Wang, Guangfa,Zhang, Jiajie,Wu, Xiaoyun. "Bisarylureas based on 1H-Pyrazolo[3,4-d]pyrimidine Scaffold as Novel Pan-RAF inhibitors with potent anti-proliferative activities: Structure-based design, synthesis, biological evaluation & molecular modelling studies". . . Retrieved 2017/04/10.