5-(4-Bromophenyl)-4,6-dichloropyrimidine

Base Information

• Chemical Name: 5-(4-Bromophenyl)-4,6-dichloropyrimidine
• CAS No.: 146533-41-7
• Molecular Formula: C10H5BrCl2N2
• Molecular Weight: 303.973
• Hs Code.: 2933599590
• Mol file: 146533-41-7.mol

Synonyms:QC-9668;

Chemical Property of 5-(4-Bromophenyl)-4,6-dichloropyrimidine

Chemical Property:

• Melting Point: 98.0 to 102.0 °C
• Boiling Point: 368.7±42.0 °C(Predicted)
• PKA: -4.92±0.26(Predicted)
• PSA: 25.78000
• Density: 1.677±0.06 g/cm3(Predicted)
• LogP: 4.21290
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility.: Chloroform (Slightly), DMSO (Slightly)

Purity/Quality:

HPLC>99% ^*data from raw suppliers

5-(4-Bromophenyl)-4,6-dichloropyrimidine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: 5-(4-Bromophenyl)-4,6-dichloropyrimidine is a reactant used in the synthesis of Macitentan, an orally active dual endothelin receptor antagonist.
• Description: 5 - (4-Bromophenyl)-4, 6- dichloropyrimidine is a key intermediate and has a wide range of applications in the pharmaceutical and chemical fields.

Technology Process of 5-(4-Bromophenyl)-4,6-dichloropyrimidine

There total 7 articles about 5-(4-Bromophenyl)-4,6-dichloropyrimidine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 86.0%

5-(4-bromophenyl)-4,6-dihydroxypyrimidine (706811-25-8) → 5-(4-bromophenyl)-4,6-dichloropyrimidine (146533-41-7)

Guidance literature:

With trichlorophosphate; In water; N,N-dimethyl-aniline; toluene; at 30 - 100 ℃; for 5h; Temperature;

Reference yield:

2-(4-bromophenyl)-acetic acid (1878-68-8) → 5-(4-bromophenyl)-4,6-dichloropyrimidine (146533-41-7)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 94 percent / conc. HCl / Heating

2.1: LHMDS / tetrahydrofuran; hexane / -78 °C

2.2: 66 percent / tetrahydrofuran; hexane / -78 - 20 °C

3.1: 51 percent / NaOEt / ethanol / 60 °C

4.1: 67 percent / POCl₃ / 90 °C

With hydrogenchloride; sodium ethanolate; lithium hexamethyldisilazane; trichlorophosphate; In tetrahydrofuran; ethanol; hexane;

DOI:10.1016/j.bmc.2006.12.029

Reference yield:

5-(p-bromophenyl)-4,6(1H,5H)-pyrimidinedione (146533-40-6) → 5-(4-bromophenyl)-4,6-dichloropyrimidine (146533-41-7)

Guidance literature:

With trichlorophosphate;

upstream raw materials:

5-(4-bromophenyl)-4,6-dihydroxypyrimidine

Ethyl 4-bromophenylacetate

2-(4-bromophenyl)malonic acid diethyl ester

2-(4-bromophenyl)-acetic acid

Downstream raw materials:

{4-[5-(4-bromophenyl)-6-chloropyrimidin-4-ylethynyl]phenyl}dimethylamine

N-[5-(4-bromophenyl)-6-(2-hydroxyethoxy)-4-pyrimidinyl]-N'-benzyl-sulfamide

benzylsulfamic acid {5-(4-bromophenyl)-6-[2-(5-bromopyrimidin-2-yloxy)-ethoxy]-pyrimidine-4-yl}-amide

ACT-132577

Refernces

• 1、 Jagtap, Kunal M.,Niphade, Navnath C.,Gaikwad, Chandrashekhar T.,Shinde, Gorakshanath B.,Toche, Raghunath B.,Joshi, Divyesh R.,Mathad, Vijayavitthal T.. "Improved and single-pot process for the synthesis of macitentan, an endothelin receptor antagonist, via lithium amide-mediated nucleophilic substitution". . p. 653 - 661. Retrieved 2018/03/09.
• 2、 -. "AN IMPROVED PROCESS FOR THE PREPARATION OF MACITENTAN". Page/Page column 20. . Retrieved 2017/09/07.