Pyrimidine, 4-chloro-5,6-dimethyl- (7CI,9CI)

Pyrimidine, 4-chloro-5,6-dimethyl- (7CI,9CI) Property

Melting point:

215-216 °C

Boiling point:

80-82 °C(Press: 10 Torr)

Density 

1.184±0.06 g/cm3(Predicted)

storage temp. 

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

pka

1.12±0.26(Predicted)

Appearance

White to off-white Solid

Safety

HS Code 

2933599590

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.

Pyrimidine, 4-chloro-5,6-dimethyl- (7CI,9CI) Chemical Properties,Usage,Production

Synthesis

GENERAL STEPS: 4,6-Dichloro-5-methylpyrimidine (Sigma-Aldrich, item 595446, 0.50 g, 3.07 mmol) and tetrakis(triphenylphosphine)palladium(0) (0.18 g, 0.15 mmol) were dissolved in toluene (6 mL). Cesium carbonate (3 g, 9.20 mmol) was added to the mixture, followed by methylboronic acid (0.20 g, 3.37 mmol) and N,N-dimethylformamide (DMF, 1 mL). The reaction mixture was placed in a microwave reactor and heated by microwave radiation at 140°C (2 cycles of 30 min each). Upon completion of the reaction, it was cooled to room temperature and filtered. The solvent was removed under reduced pressure and the residue was dissolved in ethyl acetate (EtOAc) and washed sequentially with saturated aqueous sodium bicarbonate (NaHCO3) and brine. The organic phase was separated, dried over anhydrous sodium sulfate (Na2SO4), filtered and concentrated to afford the target product 4-chloro-5,6-dimethylpyrimidine (0.18 g, 1.26 mmol, 41% yield). The product was analyzed by ultra-performance liquid chromatography (UPLC) with a retention time (rt) of 0.53 min, and the major peaks observed were 143 ([M + 1-HCl], 100%) and 445 ([M + 1-HCl], 33%). The elemental analysis results were consistent with the theoretical calculated value (142) for C6H7ClN2.1H NMR (400 MHz, CDCl3) δ (ppm): 8.70 (s, 1H), 2.57 (s, 3H), 2.39 (s, 3H).

References

[1] Patent: WO2009/3997, 2009, A1. Location in patent: Page/Page column 20-21