650628-54-9

Basic information

• Product Name: 4-CHLORO-1-(4-METHOXYPHENYL)-1H-PYRAZOLO[3,4-D]PYRIMIDINE
• Synonyms: IFLAB-BB F1386-0045;4-CHLORO-1-(4-METHOXYPHENYL)-1H-PYRAZOLO[3,4-D]PYRIMIDINE
• CAS NO: 650628-54-9
• Molecular Formula: C₁₂H₉ClN₄O
• Molecular Weight: 260.68
• Mol File: 650628-54-9.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 360.8±42.0 °C(Predicted)
• Appearance: /
• Density: 1.44±0.1 g/cm3(Predicted)
• PKA: 1.57±0.30(Predicted)
• CAS DataBase Reference: 4-CHLORO-1-(4-METHOXYPHENYL)-1H-PYRAZOLO[3,4-D]PYRIMIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-CHLORO-1-(4-METHOXYPHENYL)-1H-PYRAZOLO[3,4-D]PYRIMIDINE(650628-54-9)
• EPA Substance Registry System: 4-CHLORO-1-(4-METHOXYPHENYL)-1H-PYRAZOLO[3,4-D]PYRIMIDINE(650628-54-9)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• Hazardous Substances Data: 650628-54-9(Hazardous Substances Data)

Usage

General Description

4-CHLORO-1-(4-METHOXYPHENYL)-1H-PYRAZOLO[3,4-D]PYRIMIDINE is a chemical compound with the molecular formula C12H9ClN4O. It is a pyrazolopyrimidine derivative that contains a chlorine atom and a 4-methoxyphenyl group. It is a heterocyclic compound with potential biological activities and may be used in pharmaceutical research and drug development. Its specific properties, uses, and potential effects on organisms or biochemical pathways would need to be further studied and determined.

Upstream product

• 5305-40-8 2,6-dichloro-pyrimidine carbaldehyde 
• 3471-32-7 4-Methoxyphenylhydrazine 
• 1429924-36-6 4,6-dichloro-5-((2-(4-methoxyphenyl)hydrazono)methyl)pyrimidine 
• 19501-58-7 4-methoxyphenylhydrazine hydrochloride 
• 1235035-27-4 1-(4-methoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4(3aH)-one 
• 650628-53-8 1-(4-methoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4(5H)-one 
• 15001-13-5 ethyl 5-amino-1-(4-methoxy)phenyl-1H-pyrazole-4-carboxylate 
• 104-94-9 4-methoxy-aniline 

Downstream Products

• 650628-52-7 4-hydrazino-1-[4-methoxyphenyl]-1H-rzl[3,4-d]pyrimidine 
• 1235035-29-6 4-(4-isopropylamino-1H-pyrazolo[3,4-d]pyrimidin-1-yl)phenol 
• 393845-13-1 4-[1-(4-methoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-yl]morpholine 
• 1235035-96-7 4-(4-((3-(4-methylpiperazin-1-yl)propyl)amino)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)phenol 
• 1235035-61-6 4-(4-(3-(dimethylamino)propylamino)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)phenol 
• 393845-22-2 C₁₈H₂₁N₅O 

Relevant articles and documents

Identification of novel GLUT inhibitors

The compound class of 1H-pyrazolo[3,4-d]pyrimidines was identified using HTS as very potent inhibitors of facilitated glucose transporter 1 (GLUT1). Extensive structure–activity relationship studies (SAR) of each ring system of the molecular framework was established revealing essential structural motives (i.e., ortho-methoxy substituted benzene, piperazine and pyrimidine). The selectivity against GLUT2 was excellent and initial in vitro and in vivo pharmacokinetic (PK) studies are encouraging.

Selective synthesis of 1-substituted 4-chloropyrazolo[3,4-d]pyrimidines

Strategies for carrying out the reaction of 4,6-dichloropyrimidine-5- carboxaldehyde with various hydrazines to generate 1-substituted 4-chloropyrazolo[3,4-d]pyrimidines in a selective and high-yielding manner are presented. For aromatic hydrazines, the reaction is performed in the absence of an external base, which promotes exclusive hydrazone formation. The hydrazones subsequently cyclize at an elevated temperature to form the desired pyrazolo[3,4-d]pyrimidine products. For aliphatic hydrazines, the reaction sequence proceeds as a single step in the presence of an external base.

N-N bond-forming cyclization for the one-pot synthesis of N-aryl[3,4-d]pyrazolopyrimidines

An efficient one-pot synthesis of N-aryl[3,4-d]pyrazolopyrimidines in good yield and under mild reaction conditions is described. By exploiting electron-deficient hydroxylamines, the substituted oxime products were formed with very high E-diastereoselectivity. The key step utilizes a cyclization reaction upon an oxime derived from hydroxylamine-O-sulfonic acid to form the N-N bond of the product.