Diethylene Glycol → HCID 18452537, Verbindung

11 g of Diethylene glycol and 0.78 g of a 60% suspension of sodium hydride in mineral oil were stirred in 200 ml of tetrahydrofuran (dried over sieves) for 15 minutes then 1.3 g of 4-chloro-5-(4-chlorophenylethynyl)-2-formamido-pyrimidine was added and the mixture was stirred at 25° C. in a dry atmosphere (drying tube) for 40 hours. The reaction mixture was then evaporated under reduced pressure at 55° C. The resulting syrup was stirred with 250 ml of ethyl acetate, 125 ml of saturated aqueous sodium bicarbonate and 125 ml of water for 15 minutes. The organic phase was washed with 250 ml of water and then 100 ml of brine. After drying over sodium sulfate, the filtered solution was combined with 16 g of Silica gel 60 (230–400 mesh) and evaporated under reduced pressure. The solids were applied to column of silica gel 60 (2.5×9.5 cm). The final height of the column was 16 cm. After eluting the column with increasing concentrations of ethyl acetate in dichloromethane, the product-rich fractions were combined and the solvent evaporated under reduced pressure. The product was recrystallized twice from ethyl acetate to give 0.75 g of the desired product, m.p. 142–143° C.

1. customThe reaction mixture was then evaporated under reduced pressure at 55° C
2. stirringThe resulting syrup was stirred with 250 ml of ethyl acetate, 125 ml of saturated aqueous sodium bicarbonate and 125 ml of water for 15 minutes
3. washThe organic phase was washed with 250 ml of water
4. dry with materialAfter drying over sodium sulfate
5. customevaporated under reduced pressure
6. washAfter eluting the column
7. temperaturewith increasing concentrations of ethyl acetate in dichloromethane
8. customthe solvent evaporated under reduced pressure
9. customThe product was recrystallized twice from ethyl acetate

ORD-Eintrag

ord-0f9a580900384169b25f7895d85f96d1

Quelldatensatz

uspto-grants-2007_04

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07205297B2