Your Location:Home >Products >Intermediates >145783-15-9

145783-15-9

  • Product Name4,6-dichloro-2-propylthiopyrimidine-5-amine
  • Molecular FormulaC7H9Cl2N3S
  • Molecular Weight238.141
  • Purity99%
Inquiry

Product Details

Quick Details

  • CasNo: 145783-15-9
  • Molecular Formula: C7H9Cl2N3S
  • Purity: 99%

Quality Manufacturer Supply Top Purity 4,6-dichloro-2-propylthiopyrimidine-5-amine 145783-15-9 with Reasonable Price

  • Molecular Formula:C7H9Cl2N3S
  • Molecular Weight:238.141
  • Vapor Pressure:0mmHg at 25°C 
  • Refractive Index:1.615 
  • Boiling Point:334.05 °C at 760 mmHg 
  • PKA:-3.46±0.12(Predicted) 
  • Flash Point:155.828 °C 
  • PSA:77.10000 
  • Density:1.445 g/cm3 
  • LogP:3.44890 

4,6-dichloro-2-propylthiopyrimidine-5-amine(Cas 145783-15-9) Usage

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.

InChI:InChI=1/C7H9Cl2N3S/c1-2-3-13-7-11-5(8)4(10)6(9)12-7/h2-3,10H2,1H3

145783-15-9 Relevant articles

Synthesis method of 4,6-dichloro-2-propylmercapto-5-aminopridine

-

Paragraph 0059-0061, (2021/06/26)

The invention discloses a synthesis meth...

Preparation method of ticagrelor intermediate

-

Paragraph 0004; 0006-0009, (2021/07/09)

The invention provides a preparation met...

Pyrimido triazole compound and medical application thereof (by machine translation)

-

Paragraph 0043; 0076-0079, (2020/05/30)

The present invention relates to a compo...

Synthesis method of ticagrelor intermediate

-

Paragraph 0056-0058, (2020/06/16)

The invention provides a synthesis metho...

145783-15-9 Process route

4,6-dichloro-5-nitro-2-(propylsulfanyl)pyrimidine
145783-14-8

4,6-dichloro-5-nitro-2-(propylsulfanyl)pyrimidine

4,6-dichloro-2-(propylsulfanyl)-5-pyrimidinamine
145783-15-9

4,6-dichloro-2-(propylsulfanyl)-5-pyrimidinamine

Conditions
Conditions Yield
With ammonium molibdate; hydrogen; hypophosphorous acid; platinum on carbon; In tert-butyl methyl ether; at 20 - 65 ℃; for 7h; under 7500.75 Torr; Product distribution / selectivity; Inert atmosphere;
100%
4,6-dichloro-5-nitro-2-(propylsulfanyl)pyrimidine; With iron; acetic acid; In methanol; at 50 ℃;
With sodium hydrogencarbonate; In water; ethyl acetate; Product distribution / selectivity;
95%
With iron; acetic acid; for 4h;
73%
With iron; acetic acid; at 20 ℃; for 4h;
73%
With hydrogen; In tert-butyl methyl ether; at 30 ℃; for 3h; under 2250.23 Torr; Product distribution / selectivity;
 
With hydrogen; platinum/vanadium on charcoal; In tert-butyl methyl ether; at 5 - 30 ℃; for 9h; under 6000.6 Torr; Product distribution / selectivity; Inert atmosphere;
 
4,6-dichloro-5-nitro-2-(propylsulfanyl)pyrimidine; With ammonia;
With iron; acetic acid;
 
With iron; acetic acid; In methanol; for 2h; Reflux;
 
With iron; acetic acid; In methanol; at 20 ℃; Reflux;
 
With iron; acetic acid; In methanol; at 20 ℃; for 2h; Reflux;
 
With methanol; iron; In acetic acid; for 2h; Reflux;
 
With iron; acetic acid; In methanol; for 2h; Reflux;
 
With iron; acetic acid; In methanol; Reflux;
 
With hydrogenchloride; iron; In ethanol; water; at 65 ℃;
0.72 g
4,6-dihydroxy-5-amino-2-(propylmercapto)pyrimidine hydrochloride
1549834-66-3

4,6-dihydroxy-5-amino-2-(propylmercapto)pyrimidine hydrochloride

4,6-dichloro-2-(propylsulfanyl)-5-pyrimidinamine
145783-15-9

4,6-dichloro-2-(propylsulfanyl)-5-pyrimidinamine

Conditions
Conditions Yield
With trichlorophosphate; for 22.5h; Time; Concentration; Reflux; Sealed tube;
96%
With trichlorophosphate; for 22.5h; Time; Sealed tube; Reflux;
96%
With N,N-diethylaniline; trichlorophosphate; Inert atmosphere; Reflux;
87%
With pyridine; trichlorophosphate; at 88 - 92 ℃; for 24h;
84%

145783-15-9 Upstream products

  • 376608-73-0
    376608-73-0

    4,6-dichloro-5-((E)-2-(4-methylphenyl)diazenyl)-2-(propylsulfanyl)pyrimidine

  • 145783-14-8
    145783-14-8

    4,6-dichloro-5-nitro-2-(propylsulfanyl)pyrimidine

  • 946855-77-2
    946855-77-2

    4,6-dichloro-5-[(E)-2-(4-phenyl)diazenyl]-2-(propylsulfanyl)pyrimidine

  • 145783-12-6
    145783-12-6

    4,6-dihydroxy-2-(propylsulfanyl)pyrimidine

145783-15-9 Downstream products

  • 376608-74-1
    376608-74-1

    2-[((3aR,4S,6R,6aS)-6-[[5-amino-6-chloro-2-(propylsulfanyl)-4-pyrimidinyl]amino]-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl)oxy]-1-ethanol

  • 640285-17-2
    640285-17-2

    6-chloro-N~4~-(4-chlorophenyl)-2-(propylthio)pyrimidine-4,5-diamine

  • 1431867-58-1
    1431867-58-1

    2-(((3aR,4S,6R,6aS)-6-(7-(benzyloxy)-5-(propylthio)-3H-[1,2,3]triazolo[4,5-d]pyrimidin-3-yl)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl)oxy)ethanol

  • 274693-25-3
    274693-25-3

    methyl (((3aR,4S,6R,6aS)-6-(7-(((1R,2S)-2-(3,4-difluorophenyl)cyclopropyl)amino)-5-(propylsulfanyl)-3H-[1,2,3]triazolo[4,5-d]pyrimidin-3-yl)-2,2-dimethyltetrahydro-3aH-cyclopenta[d](1,3)dioxol-4-yl)oxy)acetate

;