Water → HCID 57592518, Verbindung

To a cooled (−78° C.) solution of 2,4-dibromothiazole (1.22 g, 5.0 mmol) in anhydrous diethyl ether (15 ml) was added n-Butyllithium (2.2 ml of 2.5 M solution in Hexanes, 5.5 mmol) in a dropwise fashion. The mixture was maintained at this temperature, with stirring, for 1 hour before a suspension of 2-chloropyrimidine (0.85 g, 7.5 mmol) in anhydrous diethylether (15 ml) was added slowly and the resulting solution allowed to slowly warm up to room temperature. The misture was then allowed to stir at room temperature for 1 hr before being quenched with water (0.113 ml, 5.0 mmol) in THF (1.25 ml) and treated with DDQ (1.25 g, 5.4 mmol) in THF (6.25 ml). The mixture was then stirred at 25° C. for 15 minutes, cooled to 0° C., treated with hexanes (4.16 ml) then cold 2M NaOH (6.25 ml, 12.5 mmol). The organic extract was removed and remaing aqueous fraction extracted further with CH2Cl2 (3×20 ml). The organic extracts were combined, dried (MgSO4), filtered and concentrated in vacuo to give a sticky brown residue which was purified by flash chromatography (SiO2) (1:1—CH2Cl2:Hexanes going to 7:3—CH2Cl2:Hexanes) to give a white solid (1.38 g, 47.1%) corresponding to the title compound in analytically pure form. m/z (LC-MSW, ESP):278.0 [M+H]+, R/T=3.90 mins

1. temperatureThe mixture was maintained at this temperature
2. additionwas added slowly
3. stirringThe mixture was then stirred at 25° C. for 15 minutes
4. temperaturecooled to 0° C.
5. extractionThe organic extract
6. customwas removed
7. extractionextracted further with CH2Cl2 (3×20 ml)
8. dry with materialdried (MgSO4)
9. filtrationfiltered
10. concentrationconcentrated in vacuo
11. customto give a sticky brown residue which
12. customwas purified by flash chromatography (SiO2) (1:1—CH2Cl2:Hexanes going to 7:3—CH2Cl2:Hexanes)

ORD-Eintrag

ord-8d16f1292e8045c985187f9ef64767a9

Quelldatensatz

uspto-grants-2009_03

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07504397B2