Water → HCID 57592518, compound

Participants

Reaction Steps

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

Provenance & Evidence