4-Amino-6-chloropyrimidine Chemical Properties

Melting point:

215-216°C

Boiling point:

289.0±20.0 °C(Predicted)

Density 

1.437±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

DMSO

form 

Solid

pka

2.16±0.10(Predicted)

color 

Pale Yellow

InChI

InChI=1S/C4H4ClN3/c5-3-1-4(6)8-2-7-3/h1-2H,(H2,6,7,8)

InChIKey

DUKKRSPKJMHASP-UHFFFAOYSA-N

SMILES

C1=NC(Cl)=CC(N)=N1

CAS DataBase Reference

5305-59-9(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

36/37/38-22

Safety Statements 

26-36/37/39-36/37

WGK Germany 

3

Hazard Note 

Harmful

HazardClass 

IRRITANT

HS Code 

29335990

MSDS

• Language:English Provider:ALFA

4-Amino-6-chloropyrimidine Usage And Synthesis

Chemical Properties

Pale Yellow Solid

Anticancer Research

4-Amino-6-chloropyrimidine has been shown to inhibit the proliferation of cancer cells in vitro and in vivo, without affecting normal cells. 4-Amino-6-chloropyrimidine also inhibits kinase activity and protein synthesis in cancer cells. This drug has a potent inhibitory effect on cell proliferation. 

Synthesis

The general procedure for the synthesis of 4-amino-6-chloropyrimidine from 4,6-dichloropyrimidine was as follows: to a suspension of 4,6-dichloropyrimidine (3.0 g, 20 mmol) in isopropanol (40 mL) was slowly added the appropriate amine, with the rate of addition being controlled so as to maintain the internal temperature of the reaction system at no more than 40°C. The reaction mixture was stirred continuously for 1 hour at 25°C. After addition, the reaction mixture was stirred continuously at 25 °C for 1 hour. Upon completion of the reaction, water (30 mL) was added and the resulting suspension was cooled to 0 °C in an ice bath. The precipitated product was collected by filtration and washed sequentially with pre-cooled isopropanol/water solvent mixture (V/V=2:1, 50 mL) and pure water. Finally, the resulting solid product was dried under vacuum to obtain the target compound 4-amino-6-chloropyrimidine.

References

[1] Journal of Medicinal Chemistry, 2011, vol. 54, # 20, p. 7066 - 7083
[2] European Journal of Medicinal Chemistry, 2014, vol. 75, p. 11 - 20
[3] Patent: WO2012/35039, 2012, A1. Location in patent: Page/Page column 84
[4] Patent: US2012/15943, 2012, A1. Location in patent: Page/Page column 54
[5] ChemMedChem, 2017, vol. 12, # 16, p. 1390 - 1398

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