Potassium Carbonate → Hydroxide

Participants

Reaction Steps

A mixture of 0.065 g (0.17 mmole) of 4-(3-chloro-phenyl)-2-(6-formyl-benzoimidazol-1-yl)-thiazole-5-carboxylic acid amide (I.2a), 0.060 mL of N,N,N′-trimethyl-ethane-1,2-diamine, 0.10 g of sodium triacetoxyborohydride and 5 mL of dichloromethane was stirred at room temperature for 6 hours, after which 1 mL of saturated aqueous ammonium chloride solution was added. The mixture was stirred at room temperature for 30 minutes, made basic by addition of saturated potassium carbonate solution and partitioned between 30 mL of dichloromethane and 30 mL of dilute potassium carbonate solution. The aqueous layer was extracted twice with 30 mL of dichloromethane. The combined dichloromethane layers were washed with brine, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by silica gel chromatography, eluting with methanol-dichloromethane-ammonium:hydroxide (10:90:1) to give 0.041 g of 4-(3-chloro-phenyl)-2-(6-{[(2-dimethylamino-ethyl)-methyl-amino]-methyl}-benzoimidazol-1yl)-thiazole-5-carboxylic acid amide (I.6) as a light pink solid. MH+/Z=469

Provenance & Evidence