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ChemicalBook CAS DataBase List 4-CHLORO-2,6-DIMETHYLPYRIMIDINE
4472-45-1

4-CHLORO-2,6-DIMETHYLPYRIMIDINE synthesis

8synthesis methods
2,4-DIMETHYL-6-HYDROXYPYRIMIDINE

6622-92-0

4-CHLORO-2,6-DIMETHYLPYRIMIDINE

4472-45-1

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.

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Yield: 82%

Reaction Conditions:

with trichlorophosphate in toluene for 3 h;Reflux;

Steps:

1.1.7. Preparation of 4-chloro-2,6-dimethylpyrimidine
POCl3 (0.460 g, 3.0 mmol) was added to the solution of compound 13 (1.0 mmol) in 15 mL of toluene and the mixture was stirred at reflux for 3 hours. Redundant POCl3 was removed under reduced pressure and ice water (10mL) was added. The solution was adjusted to the pH 9-10 with sodium carbonate and then extracted with methyl tert-butyl ether (MTBE). The organic phase was dried over sodium sulfate, and the solvent was removed under reduced pressure to afford compound 14. (Yield: 82%) MS (ESI) (m /z) [M+H]+ 143.1.

References:

Xu, Shaoyu;An, Baijiao;Li, Yuxin;Luo, Xunbang;Li, Xingshu;Jia, Xian [Bioorganic and Medicinal Chemistry Letters,2018,vol. 28,# 10,p. 1769 - 1775] Location in patent:supporting information

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