Chloroform → 2-(Chloromethyl)(1,3)oxazolo(4,5-b)pyridine

Temperatur

80 °C

2-Amino-3-pyridinol (1.1 g, Chemical Abstracts #16867-03-1) and chloromethyltrimethylorthoformate (2.27 g) were combined in diglyme (in 21 mL) and heated at 80° C. for 6 hours. The mixture was treated with p-toluenesulfonic acid hydrate (4 mg) and heated at 80° C. for an additional 48 hours. The mixture was allowed to cool to room temperature and diluted with chloroform (40 mL) and ethanol (10 mL). The mixture was filtered and the filtrate concentrated under reduced pressure. The residue was dissolved in methanol and filtered again. The resulting filtrate was concentrated under reduced pressure to provide the title compound and then dissolved in acetonitrile (35 mL) and used as a solution in the next step. 1H NMR (CDCl3, 300 MHz) δ 4.82 (2H, s), 7.38 (dd, 1H, J=8.7, 5.4 Hz), 7.89 (dd, 1H, J=8.7, 1.5 Hz), 8.62 (dd, 1H, J=5.4, 1.5 Hz). MS (DCI/NH3) m/z 169 (M+H)+.

1. temperatureheated at 80° C. for an additional 48 hours
2. temperatureto cool to room temperature
3. filtrationThe mixture was filtered
4. concentrationthe filtrate concentrated under reduced pressure
5. dissolutionThe residue was dissolved in methanol
6. filtrationfiltered again
7. concentrationThe resulting filtrate was concentrated under reduced pressure

ORD-Eintrag

ord-46bd4969c17b4c21b8a4dc962aaadb7b

Quelldatensatz

uspto-grants-2007_06

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07235661B2