4-CHLORO-2,6-DIMETHYLPYRIMIDINE Chemical Properties

Melting point:

39-40 °C

Boiling point:

180 °C

Density 

1.184±0.06 g/cm3(Predicted)

storage temp. 

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

form 

liquid

pka

1.19±0.30(Predicted)

color 

Clear, colourless

CAS DataBase Reference

4472-45-1(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

22

HazardClass 

IRRITANT

HS Code 

2933599590

4-CHLORO-2,6-DIMETHYLPYRIMIDINE Usage And Synthesis

Synthesis

General procedure for the synthesis of 4-chloro-2,6-dimethylpyrimidines from 2,4-dimethyl-6-hydroxypyrimidines: phosphorous trichloride (POCl3, 0.460 g, 3.0 mmol) was added to a solution of 2,4-dimethyl-6-hydroxypyrimidines (1.0 mmol) in toluene (15 mL), and the mixture was stirred for 3 hours under reflux conditions. Upon completion of the reaction, excess phosphorous trichloride was removed by distillation under reduced pressure and the reaction was subsequently quenched by the addition of ice water (10 mL). The pH of the reaction mixture was adjusted to 9-10 with sodium carbonate solution and then extracted with methyl tert-butyl ether (MTBE). The organic phase was dried with anhydrous sodium sulfate and concentrated under reduced pressure to remove the solvent to afford the target product 4-chloro-2,6-dimethylpyrimidine (yield: 82%). Mass spectrometry (ESI) showed a molecular ion peak (m/z) [M + H]+ of 143.1.

References

[1] Bioorganic and Medicinal Chemistry Letters, 2018, vol. 28, # 10, p. 1769 - 1775
[2] Tetrahedron Letters, 1999, vol. 40, # 42, p. 7477 - 7478
[3] Patent: US5438058, 1995, A
[4] Patent: US6093718, 2000, A

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