3974-18-3

Basic information

• Product Name: 4,6-dichloro-5-(4-chlorophenyl)-pyriMidine
• Synonyms: 4,6-dichloro-5-(4-chlorophenyl)-pyriMidine;Macitentan impurity C
• CAS NO: 3974-18-3
• Molecular Formula: C₁₀H₅Cl₃N₂
• Molecular Weight: 259.5191
• EINECS: -0
• Mol File: 3974-18-3.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 348.9±42.0 °C(Predicted)
• Appearance: /
• Density: 1.466±0.06 g/cm3(Predicted)
• Storage Temp.: 2-8°C
• PKA: -4.92±0.26(Predicted)
• CAS DataBase Reference: 4,6-dichloro-5-(4-chlorophenyl)-pyriMidine(CAS DataBase Reference)
• NIST Chemistry Reference: 4,6-dichloro-5-(4-chlorophenyl)-pyriMidine(3974-18-3)
• EPA Substance Registry System: 4,6-dichloro-5-(4-chlorophenyl)-pyriMidine(3974-18-3)

Safety Data

• Hazardous Substances Data: 3974-18-3(Hazardous Substances Data)

Usage

Description

4,6-dichloro-5-(4-chlorophenyl)-pyrimidine is a pyrimidine derivative with the molecular formula C11H6Cl3N3. It features two chlorine atoms at the 4 and 6 positions and a 4-chlorophenyl group at the 5 position. This white to off-white crystalline powder is sparingly soluble in water but soluble in organic solvents like ethanol and acetone. Due to its potential hazards, it should be handled and stored with proper safety measures.

Uses

Used in Pharmaceutical Industry:
4,6-dichloro-5-(4-chlorophenyl)-pyrimidine serves as an intermediate in the synthesis of various pharmaceuticals. Its unique structure contributes to the development of new drugs with potential therapeutic applications.
Used in Agrochemical Industry:
4,6-dichloro-5-(4-chlorophenyl)-pyriMidine is also utilized as an intermediate in the production of agrochemicals, playing a role in the creation of substances that can protect crops and enhance agricultural productivity.
Used in Cancer Research:
4,6-dichloro-5-(4-chlorophenyl)-pyrimidine has been studied for its potential use in the treatment of certain cancers and other diseases, indicating its importance in medical research for developing novel therapeutic agents.

Upstream product

• 34402-92-1 2-(4-chlorophenyl)malonic acid dimethyl ester 
• 52449-43-1 (4-chloro-phenyl)-acetic acid methyl ester 
• 1878-66-6 4-chlorophenylacetic Acid 
• 3979-80-4 5-(4-chlorophenyl)pyrimidine-4,6-diol 

Downstream Products

• 926008-93-7 5-(4-chlorophenyl)-4,6-diiodopyrimidine 
• 926008-68-6 4-chloro-5-(4-chlorophenyl)-6-(4-dimethylaminophenylethynyl)pyrimidine 
• 394205-05-1 2-phenyl-ethenesulfonic acid [6-chloro-5-(4-chloro-phenyl)-pyrimidin-4-yl]-amide 
• 441798-36-3 C₁₉H₂₀BrClN₆O₄S 
• 441795-23-9 C₂₃H₂₀BrClN₆O₄S 
• 441795-22-8 C₁₉H₁₉ClN₄O₄S 
• 441797-27-9 C₁₇H₁₄Cl₂N₄O₂S 
• 405308-28-3 2-thiophen-2-yl-ethanesulfonic acid [6-chloro-5-(4-chloro-phenyl)-pyrimidin-4-yl]-amide 
• 146531-90-0 N-[6-chloro-5-(p-chloro-phenyl)-4-pyrimidinyl]-α,α,α-trifluoro-p-toluenesulfonamide 
• 926009-37-2 C₂₄H₂₄N₅Cl 

Relevant articles and documents

The discovery of N -[5-(4-bromophenyl)-6-[2-[(5-bromo-2-pyrimidinyl)oxy] ethoxy]-4-pyrimidinyl]- N ′-propylsulfamide (macitentan), an orally active, potent dual endothelin receptor antagonist

Starting from the structure of bosentan (1), we embarked on a medicinal chemistry program aiming at the identification of novel potent dual endothelin receptor antagonists with high oral efficacy. This led to the discovery of a novel series of alkyl sulfamide substituted pyrimidines. Among these, compound 17 (macitentan, ACT-064992) emerged as particularly interesting as it is a potent inhibitor of ETA with significant affinity for the ET B receptor and shows excellent pharmacokinetic properties and high in vivo efficacy in hypertensive Dahl salt-sensitive rats. Compound 17 successfully completed a long-term phase III clinical trial for pulmonary arterial hypertension.

Arylalkane-sulfonamides having endothelin-antagonist activity

The invention relates to novel aryl-alkane-sulfonamides and their use as active ingredients in the preparation of pharmaceutical compositions. The invention also concerns related aspects including processes for the preparation of the compounds, pharmaceutical compositions containing one or more of those compounds and especially their use as endothelin receptor antagonists.