706811-25-8

Basic information

• Product Name: 4(1H)-PyriMidinone, 5-(4-broMophenyl)-6-hydroxy-
• Synonyms: 4(1H)-PyriMidinone, 5-(4-broMophenyl)-6-hydroxy-;5-(4-broMophenyl)pyriMidine-4,6(1H,5H)-dione;5-(4-broMophenyl)-6-hydroxy- 4(1H)-PyriMidinone;5-(4-broMophenyl)pyriMidine-4,6-diol;5-(4-Bromophenyl)-6-hydroxypyrimidin-4(1H)-one;5-(4-Bromophenyl)-4,6-pyrimidinediol
• CAS NO: 706811-25-8
• Molecular Formula: C₁₀H₇BrN₂O₂
• Molecular Weight: 267.07878
• Mol File: 706811-25-8.mol
• Article Data: 10

Chemical Properties

• Appearance: /
• Density: 1.74±0.1 g/cm3(Predicted)
• Storage Temp.: 2-8°C
• PKA: 4.69±0.10(Predicted)
• CAS DataBase Reference: 4(1H)-PyriMidinone, 5-(4-broMophenyl)-6-hydroxy-(CAS DataBase Reference)
• NIST Chemistry Reference: 4(1H)-PyriMidinone, 5-(4-broMophenyl)-6-hydroxy-(706811-25-8)
• EPA Substance Registry System: 4(1H)-PyriMidinone, 5-(4-broMophenyl)-6-hydroxy-(706811-25-8)

Safety Data

• Hazardous Substances Data: 706811-25-8(Hazardous Substances Data)

Usage

Description

4(1H)-Pyrimidinone, 5-(4-bromophenyl)-6-hydroxy-, also known as 5-(4-Bromophenyl)pyrimidine-4,6-diol, is a chemical compound with a unique molecular structure that features a pyrimidinone core, a 4-bromophenyl group, and two hydroxyl groups. 4(1H)-Pyrimidinone, 5-(4-bromophenyl)-6-hydroxyexhibits specific chemical properties that make it a valuable building block in the synthesis of various pharmaceutical agents.

Uses

Used in Pharmaceutical Industry:
4(1H)-Pyrimidinone, 5-(4-bromophenyl)-6-hydroxyis used as a pharmaceutical intermediate for the preparation of Macitentan, a medication used in the treatment of pulmonary arterial hypertension. Its unique structure plays a crucial role in the development of this drug, contributing to its therapeutic effects and efficacy in managing the symptoms and progression of the disease.

InChI:InChI=1S/C10H7BrN2O2/c11-7-3-1-6(2-4-7)8-9(14)12-5-13-10(8)15/h1-5H,(H2,12,13,14,15)

Upstream product

• 93139-85-6 2-(4-bromophenyl)malonic acid diethyl ester 
• 3473-63-0 formamidine acetic acid 
• 14062-25-0 Ethyl 4-bromophenylacetate 
• 1878-68-8 2-(4-bromophenyl)-acetic acid 
• 6313-33-3 formamidine hydrochloride 
• 149506-35-4 2-(4-bromophenyl)-malonic acid dimethyl ester 
• 41841-16-1 (4-bromo-phenyl)-acetic acid methyl ester 
• 77287-34-4 formamide 
• 157134-36-6 dimethyl 2-(4-bromobenzyl)malonate 

Downstream Products

• 146533-41-7 5-(4-bromophenyl)-4,6-dichloropyrimidine 
• 926008-69-7 {4-[5-(4-bromophenyl)-6-chloropyrimidin-4-ylethynyl]phenyl}dimethylamine 
• 441796-08-3 N-[5-(4-bromophenyl)-6-(2-hydroxyethoxy)-4-pyrimidinyl]-N'-benzyl-sulfamide 
• 441796-09-4 benzylsulfamic acid {5-(4-bromophenyl)-6-[2-(5-bromopyrimidin-2-yloxy)-ethoxy]-pyrimidine-4-yl}-amide 
• 1103522-45-7 ACT-132577 
• 1393813-42-7 N-5-(4-bromophenyl)-6-chloro-4-pyrimidinyl-N‘-propylsulfamide 
• 1393813-43-8 N‐[5‐(4‐bromophenyl)‐6‐[2‐hydroxyethoxy]‐4‐pyrimidinyl]‐N‐propylsulfamide 
• 441797-83-7 C₁₂H₁₂BrClN₄O₂S 
• 441797-82-6 C₁₃H₁₂BrClN₄O₂S 
• 441796-12-9 C₁₄H₁₇BrN₄O₄S 
• 441797-01-9 C₁₅H₁₇BrN₄O₄S 

Relevant articles and documents

Preparation method of 5-(4-bromophenyl)-4,6-dichloropyrimidine

The invention belongs to the technical field of pharmaceutical chemistry synthesis, and relates to a preparation method of 5-(4-bromophenyl)-4,6-dichloropyrimidine. The preparation method comprises the following steps: carrying out catalytic esterification on bromophenylacetic acid to prepare methyl p-bromophenylacetate, then carrying out a reaction with dimethyl carbonate to synthesize 2-(4-bromophenyl)-malonic acid-1,3-diethyl ester, carrying out cyclization by using formamidine hydrochloride to obtain 5-(4-bromophenyl)-4,6-dihydroxy pyrimidine, and then carrying out chlorination to obtain the product 5-(4-bromophenyl)-4,6-dichloropyrimidine. In the preparation process of the intermediate 1, a solid acid is adopted as a catalyst, so that the synthesis process and a post-treatment step are simplified. The solid acid is easy to separate and can be repeatedly used, so that resources are saved, and production cost is reduced. In a process of preparing the intermediate 2, sodium methoxideis adopted as an alkali to replace sodium hydride or amino sodium used in the prior art, so that production safety is improved, and production cost is reduced. Meanwhile, the intermediate 3 is prepared by adopting a one-pot method, so that operation steps are reduced.

Improved and single-pot process for the synthesis of macitentan, an endothelin receptor antagonist, via lithium amide-mediated nucleophilic substitution

Abstract: An improved, simple, efficient, and telescoped synthesis of macitentan, an endothelin receptor antagonist, starting from 5-(4-bromophenyl)-4,6-dichloropyrimidine in an overall yield of around 62% is described. Graphical abstract: [Figure not available: see fulltext.].

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.