150728-08-8

Basic information

• Product Name: 5-(2-Methoxyphenoxy)-2-(pyridin-4-yl)pyriMidine-4,6(1H,5H)-dione
• Synonyms: 5-(2-Methoxyphenoxy)-2-(pyridin-4-yl)pyriMidine-4,6(1H,5H)-dione;5-(o-Methoxyphenoxy)-4,6-dihydroxy-2-(4-pyridyl)pyriMidine;5-(o-methoxyphenoxy)-4,6-dihydroxy-2-(pyridin-4-yl)-pyrimidine
• CAS NO: 150728-08-8
• Molecular Formula: C₁₆H₁₃N₃O₄
• Molecular Weight: 311.29212
• Mol File: 150728-08-8.mol
• Article Data: 4

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 5-(2-Methoxyphenoxy)-2-(pyridin-4-yl)pyriMidine-4,6(1H,5H)-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 5-(2-Methoxyphenoxy)-2-(pyridin-4-yl)pyriMidine-4,6(1H,5H)-dione(150728-08-8)
• EPA Substance Registry System: 5-(2-Methoxyphenoxy)-2-(pyridin-4-yl)pyriMidine-4,6(1H,5H)-dione(150728-08-8)

Safety Data

• Hazardous Substances Data: 150728-08-8(Hazardous Substances Data)

Upstream product

• 100-48-1 pyridine-4-carbonitrile 
• 20730-58-9 2-(2-Methoxyphenoxy)propanedioic acid diethyl ester 
• 6345-27-3 4-amidinopyridine hydrochloride 
• 38768-62-6 methyl (2-methoxyphenoxy) ethanoate 
• 33278-46-5 isonicotinamidine 
• 150726-89-9 (2-methoxyphenoxy)-malonic acid dimethyl ester 
• 1878-85-9 (2-methoxyphenoxy)acetic acid 

Downstream Products

• 441797-50-8 C₂₃H₂₀ClN₅O₄S 
• 441795-81-9 C₂₅H₂₅N₅O₆S 
• 346671-43-0 4-tert-butyl-N-[6-(4-hydroxy-2-butynyloxy)-5-(o-methoxyphenoxy)-2-(pyridin-4-yl)-4-pyrimidinyl]-benzene sulfonamide 
• 346671-41-8 5-isopropyl-N-[6-(4-hydroxy-2-butynyloxy)-5-(o-methoxyphenoxy)-2-(4-pyridyl)-4-pyrimidinyl]-2-pyridine sulfonamide 
• 346671-42-9 4-tert-butyl-N-[6-chloro-5-(2-methoxy-phenoxy)-2-(pyridin-4-yl)-pyrimidin-4-yl]-benzenesulfonamide 
• 329923-33-3 5-isopropyl-pyridine-2-sulfonic acid [6-chloro-5-(2-methoxy-phenoxy)-2-pyridin-4-yl-pyrimidin-4-yl]-amide 
• 150727-72-3 4,6-dichloro-5-(o-methoxyphenoxy)-2-(pyridin-4-yl)-pyrimidine 

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.

Process for the manufacture of 2,5-disubstituted pyridines

The present invention concerns a process for the preparation of a 2,5 disubstituted pyridine of the formula (I) which comprises the steps of a) reacting a compound of the formula (II)R1-CH=CH-R2(II)with an acrylic compound of the formula (III) to form a c