Isopropanol → 4-CHLORO-6-ISOPROPOXYPYRIMIDINE

In 3.5 ml of tetrahydrofuran was suspended 0.11 g of sodium hydride (60% in oil), to which 0.5 ml of tetrahydrofuran containing 0.12 g of isopropyl alcohol dissolved therein was added dropwise at 0° C., followed by stirring for 10 minutes. To this was added dropwise 0.5 ml of tetrahydrofuran containing 0.3 g of 4,6-dichloropyrimidine dissolved therein, followed by stirring at 0° C. for 2 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, dried over anhydrous magnesium sulfate, and then concentrated. The residue was subjected to silica gel column chromatography to give 0.26 g of 4-chloro-6-isopropyloxypyrimidine.

1. additiontherein was added dropwise at 0° C.
2. dissolutiondissolved
3. stirringby stirring at 0° C. for 2 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
7. concentrationconcentrated

ORD record

ord-7ce009da07124c0daa39a20e579000b3

Source dataset

uspto-grants-2007_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07223769B2