2,4-dichloro-6-phenylpyrimidine

2,4-dichloro-6-phenylpyrimidine Property

Melting point:

92-93℃

Boiling point:

361.2±22.0 °C(Predicted)

Density 

1.363±0.06 g/cm3(Predicted)

storage temp. 

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

form 

powder to crystal

pka

-3.45±0.30(Predicted)

color 

White to Light yellow

CAS DataBase Reference

26032-72-4

Safety

HS Code 

2933.59.9500

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

2,4-dichloro-6-phenylpyrimidine Chemical Properties,Usage,Production

Chemical Properties

white powder

Synthesis Reference(s)

The Journal of Organic Chemistry, 53, p. 4137, 1988 DOI: 10.1021/jo00252a057

Synthesis

Step 2: Synthesis of 2,4-dichloro-6-phenylpyrimidine; in 50.0 ml of reaction system. To a round-bottomed flask equipped with a magnetic stirrer and a reflux condenser, protected by argon, 6-phenylpyrimidine-2,4(1H,3H)-dione (2.22 g, 11.8 mmol) and phosphorus trichloride (11.0 ml, 118 mmol) were added. The flask was placed in an oil bath preheated to 116 °C and rapidly heated to reflux. The reaction mixture was stirred at 116 °C for 4 h in an argon atmosphere and subsequently cooled to room temperature. The reaction progress was monitored by LC-MS (m/e 225 [M + H]+) to confirm product generation. Subsequently, a short-range distillation unit was installed to remove the excess phosphorus trichloride by decompression distillation at 116 °C. The residue was further distilled at ~70 °C to remove unreacted feedstock. The crude product was cooled to -3°C (using an ice bath and monitoring the temperature via a built-in thermometer). The reaction was quenched by the slow addition of ice water while keeping the temperature below 10°C. The reaction mixture was continued to be stirred in an ice bath for 60 minutes to induce precipitation of the product. The precipitate was collected by vacuum filtration and analyzed by LC-MS and confirmed to be the target product 2,4-dichloro-6-phenylpyrimidine (1.74 g, 7.7 mmol, 65% yield). m/e MS (ES) 225 [M + H]+.

References

[1] Patent: WO2009/97474, 2009, A1. Location in patent: Page/Page column 35
[2] Yakugaku Zasshi, 1950, vol. 70, p. 137
[3] Chem.Abstr., 1950, p. 5886
[4] Journal of Medicinal Chemistry, 2011, vol. 54, # 2, p. 510 - 524