4,6-Dichloro-5-(2-methoxyphenoxy)-2,2'-bipyrimidine Chemical Properties

Melting point:

157.0 to 161.0 °C

Boiling point:

520.7±60.0 °C(Predicted)

Density 

1.418±0.06 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

solubility 

DMSO (Slightly), Methanol (Slightly)

pka

-3.58±0.33(Predicted)

form 

Solid

color 

White to Light Brown

InChI

InChI=1S/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

InChIKey

IZGOBGVYADHVKH-UHFFFAOYSA-N

SMILES

C1(C2=NC=CC=N2)=NC(Cl)=C(OC2=CC=CC=C2OC)C(Cl)=N1

CAS DataBase Reference

150728-13-5(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

HS Code 

2935909550

4,6-Dichloro-5-(2-methoxyphenoxy)-2,2'-bipyrimidine Usage And Synthesis

Chemical Properties

Brown solid

Uses

Bosentan USP Related Compound D

Synthesis

General procedure for the synthesis of 4,6-dichloro-5-(2-methoxyphenoxy)-[2,2'-dipyrimidin]-4,6(1H,5H)-dione from 5-(2-methoxyphenoxy)-[2,2'-dipyrimidin]: Example of implementation: 1. 343.70 g of phosphoryl chloride was added to a reactor followed by 175.0 g of 5-(2-methoxyphenoxy)-[2,2'-dipyrimidin]-4,6(1H,5H)-dione (Compound 1). 2. The reaction mixture was heated to reflux temperature and stirred under reflux conditions for 4.0 hours. The reaction process was monitored by HPLC. 3. Upon completion of the reaction, the reaction mixture was slowly cooled to 40-50 °C. The reaction mixture was then cooled at 5-10 °C. The reaction mixture was then cooled at 5-10 °C. 4. The reaction mixture was quenched by slowly pouring into 2.625 liters of water at 5-10 °C. 5. the reaction mixture was continued to be stirred at 5-10 °C for 2.0 hours. 6. the reaction mixture was filtered and the wet filter cake was washed three times with 175.0 mL of water. 7. The wet filter cake was collected to give 4,6-dichloro-5-(2-methoxyphenoxy)-2,2'-dipyrimidine (Compound 2) with a wet weight of 255 g. The reaction was carried out at 55° C. The wet filter cake was washed three times with 175.0 mL of water. 8. The wet filter cake was dried under vacuum at 55-60°C for 8.0 hours. 9. After drying, 182 g of Compound 2 was obtained in 93% yield and >98% HPLC purity.

References

[1] Patent: US2012/136015, 2012, A1. Location in patent: Page/Page column 7
[2] Patent: CN104193687, 2017, B. Location in patent: Paragraph 0133; 0134
[3] Patent: US2008/242687, 2008, A1. Location in patent: Page/Page column 32; 34
[4] Chimia, 1996, vol. 50, # 11, p. 538 - 543
[5] Bioorganic and Medicinal Chemistry Letters, 1997, vol. 7, # 17, p. 2223 - 2228

4,6-Dichloro-5-(2-methoxyphenoxy)-2,2'-bipyrimidine(150728-13-5)Related Product Information

• 3-Methoxyphenethylamine
• 4-Methoxybenzyl cyanide
• 4-Methoxybenzyl alcohol
• Dichloroacetic acid
• 4-Methoxybenzoic acid
• p-Anisaldehyde
• (Trifluoromethoxy)benzene
• 4-Methoxybenzoyl chloride
• Anisole
• 3-Methoxyacetophenone
• 4-tert-Butylbenzenesulfonamide
• BenzenesulfonaMide, N,N'-[1,2-ethanediylbis[oxy[5-(2-Methoxyphenoxy)[2,2'-bipyriMidine]-6,4-diyl]]]bis[4-(1,1-diMethylethyl)-
• 4-tert-Butyl-N-(6-chloro-5-(2-methoxyphenoxy)-2,2'-bipyrimidin-4-yl)benzenesulfonamide
• BenzenesulfonaMide, N-[1,6-dihydro-5-(2-Methoxyphenoxy)-6-oxo[2,2'-bipyriMidin]-4-yl]-4-(1,1-diMethylethyl)-
• Bosentan Related Compound 4
• Bosentan Impurity 15 HCl
• Bosentan Related Compound 5
• Bosentan