2-Chloropyrimidine-5-carbonitrile Chemical Properties

Melting point:

130-132 °C

Boiling point:

331.3±15.0 °C(Predicted)

Density 

1.43±0.1 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

pka

-4.13±0.22(Predicted)

Appearance

Light brown to yellow Solid

InChI

InChI=1S/C5H2ClN3/c6-5-8-2-4(1-7)3-9-5/h2-3H

InChIKey

FXQSUQZXESNFNH-UHFFFAOYSA-N

SMILES

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

Safety Information

HS Code 

2933399990

2-Chloropyrimidine-5-carbonitrile Usage And Synthesis

Uses

2-Chloro-5-cyanopyrimidine is a pyrimidine derivative and can be used as an important pharmaceutical intermediate for cancer treatment.

Synthesis

To a stirring solution of 2-aminopyrimidine-5 -carbonitrile (1.0 g, 8.33 mmol) in CH3CN (15 ml) at room temperature under Argon added copper (II) chloride (1.679 g, 12.5 mmol) and test-butyl nitrite (1.288 g, 12.5 mmol). The reaction mixture was placed under Argon in a preheated oil bath (60 ℃). The reaction mixture was cooled to room temperature, and 20 ml of ether was added. The resulting insoluble material was filtered, and the filtrate was concentrated. The crude product was dissolved in a small amount of DCM (~2 ml) and loaded onto a 40 g ISCO silica gel column which was eluted with a 20 min gradient from 0% to 100% EtOAc/Hexanes. 723 mg (61%) of 2-chloropyrimidine-5-carbonitrile was obtained as a tan solid.

References

[1] Patent: US2017/170419, 2017, A1. Location in patent: Paragraph 0041
[2] Patent: WO2010/9183, 2010, A1. Location in patent: Page/Page column 104-105
[3] Patent: WO2008/110611, 2008, A1. Location in patent: Page/Page column 37

2-Chloropyrimidine-5-carbonitrile(1753-50-0)Related Product Information

• triflumezopyrim
• Trichloropyrimidine
• 2-Amino-4-chloro-6-methoxypyrimidine
• 2,4,5-Trichloropyrimidine
• Ethyl 2-chloropyrimidine-5-carboxylate
• 5-CYANOPYRIMIDINE
• 2,4-Dichloro-5-cyanopyrimidine
• 4-AMINO-2-CHLOROPYRIMIDINE-5-CARBONITRILE
• AURORA KA-6205
• 2,4,6-TRICHLORO-5-CYANOPYRIMIDINE
• 5-Pyrimidinecarbonitrile, 2-chloro- (7CI,8CI)