5-fluoropyriMidine-2-carbaldehyde

5-fluoropyriMidine-2-carbaldehyde Property

Boiling point:

272.3±32.0 °C(Predicted)

Density 

1.374±0.06 g/cm3(Predicted)

storage temp. 

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

pka

-2.22±0.22(Predicted)

Appearance

Orange to red Solid

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

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.

5-fluoropyriMidine-2-carbaldehyde Chemical Properties,Usage,Production

Synthesis

General procedure for the synthesis of 5-fluoropyrimidine-2-carbaldehyde from 2-cyano-5-fluoropyrimidine: To an anhydrous THF solution of 5-fluoropyrimidine-2-carbonitrile (1.0 g, 8.1 mmol) was slowly added a solution of DIBAL-H (8.1 mL) over a period of 20 min at -78 °C. The reaction mixture was continued to be stirred at this temperature for 2 h. The reaction was subsequently quenched by the addition of MeOH. The reaction system was slowly warmed to room temperature and then concentrated HCl solution was added. The resulting mixture was stirred at room temperature for 2 h before being extracted with an aqueous layer and EtOAc (3 times). The combined organic phases were washed with brine and dried over MgSO4. The solvent was removed by concentration under reduced pressure to give 5-fluoropyrimidine-2-carbaldehyde (780 mg, 76% yield). Mass spectrometry result: [M+H]+ 127.

References

[1] Patent: WO2007/49041, 2007, A1. Location in patent: Page/Page column 71
[2] Patent: WO2008/117050, 2008, A1. Location in patent: Page/Page column 64
[3] Patent: WO2008/135786, 2008, A1. Location in patent: Page/Page column 53
[4] Patent: WO2013/142269, 2013, A1. Location in patent: Paragraph 0645; 0646; 0647