Potassium Carbonate → (S)-1-(5-bromopyrimidin-2-yl)ethanol

Temperatur

85 °C

(Z)-2-bromo-3-(dimethylamino)prop-2-enal (11.5 g), potassium carbonate (13.4 g), ethanol (200 mL) and 2-hydroxy-2-methyl-propanamidine hydrochloride (12.1 g) were placed in a flask and the mixture heated at 85° C. overnight. The reaction mixture was cooled and the mixture filtered, washed with ethanol and the combined filtrates concentrated in vacuo with silica gel. This residue was purified by chromatography on silica, eluting with 0-50% ethyl acetate in heptane to give (1S)-1-(5-bromopyrimidin-2-yl)ethanol as a white solid (2.1 g, 16%). 1H NMR (CDCl3) δ 8.83 (s, 2H), 4.98 (m, 1H), 3.8 (m, 1H), 1.6 (d, J=6.6 Hz, 3H). Chiral HPLC: Column. Chirapak IC, 0.46 cm×25 cm; 20 min isocratic gradent; 5:95 EtOH:n-hexane+0.1% diethylamine) retention time=14.08 min. (racemic mixture: ˜14.5 min: S isomer; ˜17.5 min: R isomer).

1. temperatureThe reaction mixture was cooled
2. filtrationthe mixture filtered
3. washwashed with ethanol
4. concentrationthe combined filtrates concentrated in vacuo with silica gel
5. customThis residue was purified by chromatography on silica
6. washeluting with 0-50% ethyl acetate in heptane

ORD-Eintrag

ord-eedb5706b2a841bf8e35ee149a0c0812

Quelldatensatz

uspto-grants-2014_12

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08906902B2