Triethylamine → 6-bromo-1H,2H,4H-pyrido(2,3-d)(1,3)oxazin-2-one

Temperatur

0 °C

A mixture of 2-amino-5-bromo-3-hydroxymethylpyridine hydrobromide (Apollo, Cheshire, UK, 0.528 mmol) in dichloromethane (1.25 ml) and triethylamine (1.162 mmol) was cooled with an ice-bath. Was added to the RM trichloromethyl chloroformate (0.317 mmol) in dichloromethane and the RM was stirred for 30 min at 0° C. and 1 h at rt. The RM was diluted with dichloromethane, washed with saturated aqueous NaHCO3, dried over Na2SO4, filtered and evaporated. The residue was absorbed on silica gel and separated by flash chromatography (heptane/EtOAc 0% to 80%). The fractions containing product were evaporated together to give the title compound as a yellow solid. (HPLC: tR 2.16 min (Method A); M+H=229, 231 MS-ES)

1. temperaturewas cooled with an ice-bath
2. washwashed with saturated aqueous NaHCO3
3. dry with materialdried over Na2SO4
4. filtrationfiltered
5. customevaporated
6. customThe residue was absorbed on silica gel
7. customseparated by flash chromatography (heptane/EtOAc 0% to 80%)
8. additionThe fractions containing product
9. customwere evaporated together

ORD-Eintrag

ord-9ee95319140d42a7bd6d5471c7ff8b3d

Quelldatensatz

uspto-grants-2013_07

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08476294B2