Water → HCID 57592518, compound

Participants

Reaction Steps

To a cooled (−78° C.) solution of 2,4-dibromothiazole (24)(0.73 g, 3.0 mmol) in anhydrous diethylether (7 ml) was added n-butyllithium (2.5M in hexane, 1.5 ml, 3.28 mmol) in a dropwise fashion via syringe. The yellow solution was stirred at −78° C. for 15 minutes before the addition of a suspension of 2-chloropyrimidine (20)(2.73 mmol, 0.313 g) in anhydrous diethylether (8 ml). The mixture was allowed to warm to room temperature and maintained like this, with stirring for 16 hours. The mixture was quenched carefully by dropwise addition of water (0.061 ml, 3.41 mmol) in THF (0.7 ml) and then DDQ (0.681 g, 3.0 mmol) added to effect aromatization. The mixture was cooled to 0° C. and 3M NaOH (aq) (2.28 ml, 6.83 mmol) added which caused a sticky solid to adhere to bottom of the reaction vessel. The solvents were collected, dried (MgSO4), filtered and concentrated in vacuo to give the title compound (0.58 g, 69.8%) in suitably clean form to be used without further purification. m/z (LC-MS, ESP): 327 [M+H]+, R/T=3.73 mins.

Provenance & Evidence