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ChemicalBook >  Product Catalog >  Pharmaceutical intermediates >  Heterocyclic compound >  Pyrimidines >  Aminopyrimidine >  4,6-dichloro-2-propylthiopyrimidine-5-amine

4,6-dichloro-2-propylthiopyrimidine-5-amine

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4,6-dichloro-2-propylthiopyrimidine-5-amine Basic information

Product Name:
4,6-dichloro-2-propylthiopyrimidine-5-amine
Synonyms:
  • 4,6-dichloro-2-propylthiopyrimidine-5-amine
  • 4,6-dichloro-2-(propylthio)-5-PyriMidinaMine
  • 4,6-Dichloro-2-(propylthio)pyrimidin-5-amine
  • Tecagrelor InterMediate 3
  • 5-PyriMidinaMine, 4,6-dichloro-2-(propylthio)-
  • 4,6-dichloro-2-(propylsulfanyl)-5-pyriMidinaMine
  • Ticagrelor Impurity 110
  • 4,6-Dichloro-5-amino-2-propylthiopyrimidine
CAS:
145783-15-9
MF:
C7H9Cl2N3S
MW:
238.14
EINECS:
808-051-8
Product Categories:
  • Intermediate of Ticagrelor
  • bc0001
  • 145783-15-9
Mol File:
145783-15-9.mol
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4,6-dichloro-2-propylthiopyrimidine-5-amine Chemical Properties

Boiling point:
334.1±37.0 °C(Predicted)
Density 
1.44
storage temp. 
Keep in dark place,Sealed in dry,Room Temperature
solubility 
soluble in Methanol
form 
powder to lump to clear liquid
pka
-3.46±0.12(Predicted)
color 
White or colorless to Brown
Water Solubility 
100mg/L at 22℃
InChI
InChI=1S/C7H9Cl2N3S/c1-2-3-13-7-11-5(8)4(10)6(9)12-7/h2-3,10H2,1H3
InChIKey
CJJLJBFJNXMANZ-UHFFFAOYSA-N
SMILES
C1(SCCC)=NC(Cl)=C(N)C(Cl)=N1
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Safety Information

Safety Statements 
24/25
HS Code 
29335990
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4,6-dichloro-2-propylthiopyrimidine-5-amine Usage And Synthesis

Description

4,6-dichloro-2-propylthiopyrimidine-5-amine is a pharmaceutical intermediate used in the preparation of Ticagrelor, which belongs to a class of drugs called antiplatelet agents. It works by preventing platelets (a type of blood cell) from aggregating and forming clots that can lead to heart attacks or strokes.

Chemical Properties

Light pink to dark brown liquid or semi solid

Uses

Intermediate in the preparation of Ticagrelor (T437700) and reversible P2Y12 receptor antagonists.

Synthesis

The synthesis of 4,6-dichloro-2-propylthiopyrimidine-5-amine is as follows:tert-Butyl methyl ether (370 g) was placed under nitrogen in a 1 L stainless steel autoclave equipped with a temperature-controlled jacket, an Ekato InterMIG stirrer, an internal temperature sensor and a dip pipe, and 4,6-dichloro-5-nitro-2-propylsulfanyl-pyrimidine (94.5 g, 0.35 mol) was added and dissolved at a stirring rate of 200 min-1. The catalyst suspension was prepared and transferred into the autoclave as described in the preceding example. The autoclave was sealed and the stirring rate was increased to 600 min-1 while the autoclave was purged four times with nitrogen. Subsequently, hydrogen gas feed via the dip pipe at a constant flow rate (pmax=10 bar) as well as a heating-up ramp (45 K/h) from 20° C. to 65° C. were started in parallel, while stirring at 600 min-1. The progress of the exothermic reaction was followed by recording the hydrogen uptake as well as the internal and jacket temperature curve. Upon completion of the hydrogen uptake (ca. 1.1 mol or 3 molar equivalents) after about 4 h, stirring of the reaction mixture was continued for an additional 3 hours at 65° C. After unloading the autoclave (the reactor was cooled down to 20° C., the hydrogen pressure was released and the reactor purged four times with nitrogen), the catalyst was filtered off. The autoclave as well as the filter cake (catalyst) were washed with tent-butyl methyl ether (185 g). The organic phases were combined and the water layer separated. An IPC-sample was taken to analyze the product mixture. The conversion was found to be quantitative with no nitroso or hydroxylamine intermediate being detectable.

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