2-Chloropyrimidine-4-carbonitrile Chemical Properties

Melting point:

53-55°

Boiling point:

331.3±15.0 °C(Predicted)

Density 

1.43

storage temp. 

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

form 

powder

pka

-4.96±0.20(Predicted)

color 

Off-white to faint yellow/beige

InChI

InChI=1S/C5H2ClN3/c6-5-8-2-1-4(3-7)9-5/h1-2H

InChIKey

HXVQPZSXXYOZMP-UHFFFAOYSA-N

SMILES

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

Safety Information

Hazard Codes 

Xn

Risk Statements 

22-36/37/38

Safety Statements 

26-36/37

RIDADR 

3439

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29335990

2-Chloropyrimidine-4-carbonitrile Usage And Synthesis

Application

2-Chloro-4-cyanopyrimidine can be used to prepare 2-chloropyrimidine-4-carboxylic acid, which is a key intermediate for the treatment of hyperphosphatemia and the synthesis of benzylsulfonamide pyrazole kinase inhibitors. It is widely used in the synthesis of many pharmaceutical intermediates both domestically and internationally, and has a very promising market prospect.

Chemical Properties

Light yellow solid

Synthesis Reference(s)

Journal of Heterocyclic Chemistry, 1, p. 130, 1964 DOI: 10.1002/jhet.5570010305

Synthesis

General procedure for the synthesis of 2-chloro-4-cyanopyrimidine from 2-hydroxypyrimidine-4-carbaldehyde oxime: (Step 7) A mixture of 2-oxo-1,2-dihydropyrimidine-4-carboxaldehyde oxime (72.6 g) in cold (0°C) phosphorochloride (280 ml) was placed under vigorous stirring and slowly heated until the onset of a vigorous reaction was observed, at which point heating was stopped. After the reactants were completely dissolved, N,N-diethylaniline (36.3 mL) was added and the reaction mixture continued to reflux for 30 minutes. Upon completion of the reaction, it was cooled to room temperature and the phosphoryl chloride was evaporated under reduced pressure. The crude product was quenched with ice water (500 mL) and extracted with dichloromethane (5 x 200 mL). The organic phases were combined, dried over anhydrous sodium sulfate and subsequently concentrated. The residue was purified by short silica gel column chromatography (dichloromethane as eluent). After concentration, the product 2-chloro-4-cyanopyrimidine (63 g, solidified on standing, 86.5% yield) was obtained and used directly in the next reaction.

References

[1] Patent: WO2013/39854, 2013, A1. Location in patent: Page/Page column 39
[2] Patent: WO2005/75468, 2005, A2. Location in patent: Page/Page column 43

2-Chloropyrimidine-4-carbonitrile(75833-38-4)Related Product Information

• 4-chloro-2-methoxy-6-methylpyrimidine
• 2-Chloro-4,5-diMethoxy-pyriMidine
• 2-Ethoxy-4-chlor-pyrimidin
• 2-Chloro-4-methoxy-6-methylpyrimidine
• 2-Chloro-5-Methoxy-pyriMidin-4-ylaMine
• 2-Chloro-4-methoxymethyl-pyrimidine
• 4-Pyrimidinecarbonitrile (7CI,9CI)
• 2-CHLORO-6-METHYLPYRIMIDINE-4-CARBONITRILE
• 2-Chloropyrimidine-4-carbonitrile
• 2-CHLORO-6-(4-METHOXYPHENYL)-4-PYRIMIDINECARBONITRILE