150728-13-5

Basic information

• Product Name: 4,6-Dichloro-5-(2-methoxyphenoxy)-2,2'-bipyrimidine
• Synonyms: 2,2'-Bipyrimidine, 4,6-dichloro-5-(2-methoxyphenoxy)-;2-(4,6-dichloro-5-(2-methoxyphenoxy) pyrimidin-2-yl)pyrimidine;2,2'-Bipyrimidine, 4,6-dichloro-5-(2-methoxyphenoxy)- (bosentan intermediate);4,6-Dichloro-5-(O-Methoxyphenoxy)-2-(2-Pyrimidinyl)Pyrimidine;BOSENTAN INTERMEDIATES;2,2'-Bipyrimidine,4,6-dichloro-5-(2-methoxyphenox;4,6-Dichloro-5-(o-methoxyphenoxy)-2-(2-pyrimidinyl;2-(5-(2-methoxyphenoxy)-4,6-dichloropyrimidin-2-yl)pyrimidine
• CAS NO: 150728-13-5
• Molecular Formula: C₁₅H₁₀Cl₂N₄O₂
• Molecular Weight: 349.17
• EINECS: 1806241-263-5
• Product Categories: API intermediates;pyrimidine;Aromatics;Bases & Related Reagents;Heterocycles;Nucleotides
• Mol File: 150728-13-5.mol
• Article Data: 19

Chemical Properties

• Melting Point: 157.0 to 161.0 °C
• Boiling Point: 520.7 °C at 760 mmHg
• Flash Point: 268.7 °C
• Appearance: /Solid
• Density: 1.418 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.617
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: -3.58±0.33(Predicted)
• CAS DataBase Reference: 4,6-Dichloro-5-(2-methoxyphenoxy)-2,2'-bipyrimidine(CAS DataBase Reference)
• NIST Chemistry Reference: 4,6-Dichloro-5-(2-methoxyphenoxy)-2,2'-bipyrimidine(150728-13-5)
• EPA Substance Registry System: 4,6-Dichloro-5-(2-methoxyphenoxy)-2,2'-bipyrimidine(150728-13-5)

Safety Data

• Hazard Codes: Xi
• Hazardous Substances Data: 150728-13-5(Hazardous Substances Data)

Usage

Chemical Properties

Brown solid

Uses

Bosentan USP Related Compound D

InChI:InChI=1/C15H10Cl2N4O2/c1-22-9-5-2-3-6-10(9)23-11-12(16)20-15(21-13(11)17)14-18-7-4-8-19-14/h2-8H,1H3

Upstream product

• 42839-08-7 pyrimidine-2-carboxylic acid ethyl ester 
• 57871-18-8 methyl ester of imino-pyrimidine acid 
• 329923-17-3 5-(2-methoxyphenoxy)-2-(pyrimidin-2-yl)tetrahydropyrimidine-4,6-dione 
• 14080-23-0 2-cyanopyrimidine 
• 150726-89-9 (2-methoxyphenoxy)-malonic acid dimethyl ester 
• 90-05-1 2-methoxy-phenol 
• 20730-58-9 2-(2-Methoxyphenoxy)propanedioic acid diethyl ester 
• 329923-15-1 4,6-dihydroxy-5-(o-methoxyphenoxy)-2-(2-pyrimidinyl)-pyrimidine 
• 150728-12-4 5-(2-methoxyphenoxy)-2-(pyrimidin-2-yl) pyrimidine-4,6(1H, 5H)-dione 

Downstream Products

• 147536-97-8 bosentan 
• 1174918-31-0 bosentan potassium 
• 184779-15-5 2-(5-(2-methoxy-phenoxy)-6-chloro-2-(pyrimidin-2-yl)pyrimidin-4-yloxy) ethanol 
• 150727-06-3 4-tert-butyl-N-(6-chloro-5-(2-methoxyphenoxy)2,2'-bipyrimidin-4-yl)benzene sulfonamide 
• 1040221-35-9 4-d9-tert-butyl-N-(6-chloro-5-(2-methoxyphenoxy)-2,2'-bipyrimidin-4-yl)benzenesulfonamide 
• 179400-86-3 5-isopropyl-N-[6-chloro-5-(o-methoxyphenoxy)-2-(2-pyrimidinyl)-4-pyrimidinyl]-2-pyridine sulfonamide 
• 167405-02-9 4-vinyl-N-[6-chloro-5-(2-methoxy-phenoxy-2-pyrimidin-2-yl)-pyrimidin-4-yl]-benzenesulfonamide 

Relevant articles and documents

A method for the treatment of pulmonary arterial hypertension drug preparation method

The invention provides a preparation method of a therapeutic medicine for treating pulmonary arterial hypertension and particularly provides a preparation method of a key intermediate compound as shown in a formula (IV). According to the method, the compound as shown in the formula (IV) is obtained by means of reaction of a compound as shown in a formula (II) and a compound as shown in a formula (III). The preparation method is easily available in raw materials, low in cost, mild in condition and suitable for industrialized production. The formulae (IV), (II) and (III) are as shown in the specification.

Metabolism study and biological evaluation of bosentan derivatives

Bosentan, the first-in-class drug used in treatment of pulmonary arterial hypertension, is principally metabolized by the cytochromes P450, and it is responsible for cytochromes induction and drug-drug interaction events with moderate to severe consequences. A strategy to reduce drug-drug interactions consists of increasing the metabolic stability of the perpetrator, and fluorinated analogues are often designed to block the major sites of metabolism. In this paper bosentan analogues were synthesized, and their metabolism and biological activity were evaluated. All synthesized compounds showed an improved metabolic stability towards CYP2C9, with one maintaining a moderate antagonist effect towards the ETA receptor.

ACID ADDITION SALTS OF BOSENTAN

The present invention relates to the stable acid addition salts of Bosentan that are useful for the purification of Bosentan base. In particular, the Bosentan acid addition salt is selected from Bosentan citrate and Bosentan tartrate.