Ethanol → 5-Ethoxypyrimidine

Sodium (2.89 g. 125.8 mmol) was dissolved in ethanol (110 mL) and 5-bromopyrimidine (10.0 g, 62.9 mmol) added. The reaction was heated at 120° in an autoclave for 17 h and then allowed to stand at 23° for 60 h. The ethanol was removed under reduced pressure and water (5 mL) added to the concentrate. The aqueous phase was extracted with CH2Cl2 (4×100 mL). The combined organic extracts were washed with saturated NaCl solution, dried with anhydrous K2CO3, filtered, and concentrated under reduced pressure. Silica gel chromatography (Hexane/EtOAc; 70:30) of the concentrate yielded 5-ethoxypyrimidine (2.00 g, 25.6%).

1. temperatureThe reaction was heated at 120° in an autoclave for 17 h
2. customThe ethanol was removed under reduced pressure and water (5 mL)
3. additionadded to the concentrate
4. extractionThe aqueous phase was extracted with CH2Cl2 (4×100 mL)
5. washThe combined organic extracts were washed with saturated NaCl solution
6. dry with materialdried with anhydrous K2CO3
7. filtrationfiltered
8. concentrationconcentrated under reduced pressure

ORD record

ord-77972697092b4fd59903f046ff5a45d4

Source dataset

uspto-grants-1995_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05434154