Basic information Uses Safety Supplier Related
ChemicalBook >  Product Catalog >  Pharmaceutical intermediates >  Heterocyclic compound >  Pyrimidines >  5-(4-Bromophenyl)-4,6-dichloropyrimidine

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

Basic information Uses Safety Supplier Related

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

Product Name:
5-(4-Bromophenyl)-4,6-dichloropyrimidine
Synonyms:
  • PyriMidine, 5-(4-broMophenyl)-4,6-dichloro-
  • 5-(4-broMophenyl)-4,6-dichloropyriMidine
  • 5-(4-Bromophenyl)-4,6-dichloro-Pyrimidin
  • 5-(4-broMophenyl)-4
  • Macitentan Intermediate 1
  • 5-(4-Bromophenyl)-4,6-dichloropyrimidine(146533-41-7)
  • Macitentan Impurity 26
  • potassiuM (N-propylsulfaMoyl)aMide
CAS:
146533-41-7
MF:
C10H5BrCl2N2
MW:
303.97
Product Categories:
  • 146533-41-7
Mol File:
146533-41-7.mol
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5-(4-Bromophenyl)-4,6-dichloropyrimidine Chemical Properties

Melting point:
98.0 to 102.0 °C
Boiling point:
368.7±42.0 °C(Predicted)
Density 
1.677±0.06 g/cm3(Predicted)
storage temp. 
under inert gas (nitrogen or Argon) at 2-8°C
solubility 
Chloroform (Slightly), DMSO (Slightly)
form 
Solid
pka
-4.92±0.26(Predicted)
color 
Off-White
Sensitive 
Light Sensitive
InChI
InChI=1S/C10H5BrCl2N2/c11-7-3-1-6(2-4-7)8-9(12)14-5-15-10(8)13/h1-5H
InChIKey
WEEFLZORZXLIJE-UHFFFAOYSA-N
SMILES
C1=NC(Cl)=C(C2=CC=C(Br)C=C2)C(Cl)=N1
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Safety Information

HS Code 
2933599590
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5-(4-Bromophenyl)-4,6-dichloropyrimidine Usage And Synthesis

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.

Uses

5-(4-Bromophenyl)-4,6-dichloropyrimidine is a reactant used in the synthesis of Macitentan, an orally active dual endothelin receptor antagonist.

Synthesis


Dimethyl 2-(4-bromophenyl) malonate (6) A solution of methyl 2-(4-bromophenyl)acetate (5) (206.8 g, 0.9 mol) in THF (400mL), then it was added drop-wise to a suspension of sodium hydride (65.0 g,2.71 mol) in THF solution(1000mL) at room temperature, control the drip rate and the temperature was kept 25 ~ 27 , when dropping ?? was completed, keep the temperature for 1h, then dimethyl carbonate (DMC) (325.1 g, 3.6 mol) was added, keep the reaction for 14 h. After cooling to -10 , the s ?? olution is adjusted to pH 6~7 using hydrochloric acid (36%) then removed THF under reduced pressure, ethyl acetate (1600mL) was added to the solution, the organic phase was washed with hydrochloric acid solution (1 mol/L, 36%) saturated brine and was dried by magnesium sulfate, then it was distilled under reduced pressure to afford yellow oil. The yellow oil was solidified by cyclohexane, after mixture was filtered and driedto obtain yellow solid, then re-crystallized with ethanol- acetone (5:2) to obtain 6 as white solid (192.9 g).yield: 72.3%. M.p.77-79 , ?? MS; 308.8 [M + Na] + , 596.7[2M+Na]+ .
5-(4-Bromophenyl) pyrimidine-4, 6-diol (7) Sodium (46.9g, 2.0mol) was slowly added into methanol (600mL) at 0 . Dimethyl ?? ¨C 2 - ( 4 ¨Cbromophenyl ) malonate(192.9g,0.67mol) was dissolved in methanol (380mL) added into the solution of sodium methoxide, after dropping, keep the reaction for 1h at roo was added, heated to 40 for 3.5 h. After cooling to room temperature, methanol was ?? distilled off under reduced pressure, the solution of citric acid was added into the residue and stirred for 1 hours. The precipitated solid was suction filtered, and the solid w m temperature, then formamidineas washed with water, then dried to give a yellow solid. The crude product was added into cyclohexane (900mL) was stirred for 3h at room temperature, then the precipitated solid was suction filtered, the solid was washed with cyclohexane and dried to obtain7 as light yellow solid (149.1 g ,84.4%). M.p.178-180 ??; MS; 269.0[M+H] + , 288.9[M + Na] + .
5-(4-Bromophenyl)-4, 6-dichloropyrimidine (1) 5-(4-Bromophenyl) pyrimidine-4, 6-diol (53.4g, 0.2mol) was slowly added into POCl3 (427mL), refluxed for 8h. POCl3 was distilled off under reduced pressure, then the black viscous residue was poured into ice water (1000mL), The solution was adjusted to pH9~10 using potassium carbonate. The product was filtered off, washed with water and dried under reduced pressure to afford 5-(4-bromophenyl)-4, 6-dichloropyrimidine (1) as white solid (52.6 g, 86.5%). M. P. 101 -102 , ?? MS: 302 [M+H] + ; 1 H -NMR (300 MHz, DMSO-d 6 ) |? 8.96(s, 1H,Ar-H), 7.72(d, J = 8.5 Hz, 2H, Ar-H), 7.39(d, J = 8.5Hz, 2H, Ar-H).

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