2,4,5-Trichloropyrimidine Chemical Properties

Boiling point:

84°C 1mm

Density 

1.6001 g/mL at 25 °C (lit.)

refractive index 

n20/D 1.574(lit.)

Flash point:

>230 °F

storage temp. 

Inert atmosphere,Store in freezer, under -20°C

form 

clear liquid

pka

-4.26±0.29(Predicted)

color 

Colorless to Light orange to Yellow

Water Solubility 

Not miscible or difficult to mix in water.

BRN 

4449

InChI

InChI=1S/C4HCl3N2/c5-2-1-8-4(7)9-3(2)6/h1H

InChIKey

GIKMWFAAEIACRF-UHFFFAOYSA-N

SMILES

C1(Cl)=NC=C(Cl)C(Cl)=N1

CAS DataBase Reference

5750-76-5(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

RIDADR 

3267

WGK Germany 

3

Hazard Note 

Irritant

HazardClass 

8

PackingGroup 

III

HS Code 

29335990

MSDS

• Language:English Provider:2,4,5-Trichloropyrimidine
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

2,4,5-Trichloropyrimidine Usage And Synthesis

Chemical Properties

Colorless to pale yellow liquid

Uses

2,4,5-Trichloropyrimidine is used in the synthesis of potent and selective anaplastic lymphoma kinase (ALK-5) inhibitors, used as an anti-tumor treatment. Also used in the synthesis of EGFR inhibitors.

Synthesis

General procedure for the synthesis of 2,4,5-trichloropyrimidine from 5-chlorouracil: 5-chlorouracil (4.5 g, 30.82 mmol) was dissolved in phosphorochloridic acid (100 mL), followed by phosphorus pentachloride (19.2 g, 92.46 mmol). The reaction mixture was heated to reflux overnight; after completion of the reaction, it was cooled to room temperature and the solvent was removed by evaporation under reduced pressure. The residue was cooled to 0 °C and crushed ice was added slowly. The mixture was stirred for 10 min and partitioned between water and dichloromethane (DCM). The organic phase was separated and washed three times with water. The aqueous layer was combined and extracted twice with DCM. The combined organic extracts were dried over anhydrous sodium sulfate (Na2SO4), filtered and the solvent was evaporated under reduced pressure to give 2,4,5-trichloropyrimidine as a yellow oil, which did not require further purification.

References

[1] Patent: WO2008/28860, 2008, A1. Location in patent: Page/Page column 45
[2] Patent: US2006/25433, 2006, A1. Location in patent: Page/Page column 108
[3] Patent: US4299961, 1981, A
[4] Patent: WO2008/79719, 2008, A1. Location in patent: Page/Page column 43-44; 47-48; 49; 51
[5] Patent: WO2007/120339, 2007, A1. Location in patent: Page/Page column 39-42

2,4,5-Trichloropyrimidine(5750-76-5)Related Product Information

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