4-Methyl-2-Pentanol → 4-Chloro-6-(1,3-dimethylbutoxy)pyrimidine

In 4 ml of tetrahydrofuran was suspended 0.11 g of sodium hydride (60% in oil), to which 0.5 ml of a solution containing 0.23 g of 4-methyl-2-pentanol in tetrahydrofuran was added dropwise at room temperature, followed by stirring for 10 minutes. To this was added dropwise 0.5 ml of a solution containing 0.3 g of 4,6-dichloropyrimidine in tetrahydrofuran at 0° C., followed by stirring at the same temperature for 2 hours and further stirring at room temperature for 4 hours. The reaction mixture was then poured into a saturated aqueous ammonium chloride solution, which was extracted three times with t-butyl methyl ether. The combined organic layers were washed with a saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate to give a crude product of 4-chloro-6-(1,3-dimethylbutoxy)pyrimidine.

1. additionwas added dropwise at room temperature
2. stirringby stirring at the same temperature for 2 hours
3. stirringfurther stirring at room temperature for 4 hours
4. extractionwas extracted three times with t-butyl methyl ether
5. washThe combined organic layers were washed with a saturated aqueous sodium chloride solution
6. dry with materialdried over anhydrous magnesium sulfate

ORD record

ord-74b9d48244c84a34a78b2264f286262c

Source dataset

uspto-grants-2007_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07223769B2