Chloroacetyl chloride → 5-Amino-3-(3,5-dimethylphenyl)-2-(4-pyridyl)-7H-thiazolo[3,2-a]pyrimidin-7-one

Participants

Reaction Conditions

Reaction Steps

To a solution of [4-(3,5-dimethylphenyl)-5-(4-pyridyl)-1,3-thiazol-2-yl)amine (1.0 g) in N,N-dimethylacetamide (10 mL) was added chloroacetyl chloride (0.60 g) and the mixture was stirred at 80° C. for 14 hours. N,N-Dimethylacetamide was distilled off under reduced pressure and the resultant residue was dissolved in dimethylsulfoxide (5 mL). To this solution was added sodium cyanate (0.24 g) and the mixture was stirred at room temperature for 14 hours. An aqueous solution of sodium hydrogen carbonate was added to the reaction mixture and the mixture was extracted with a mixed solvent of ethyl acetate-tetrahydrofuran (1:1). The extract was washed with brine, dried over anhydrous sodium sulfate and filtered. The solvent was concentrated under reduced pressure and the residue was purified by silica gel column chromatography (hexane-tetrahydrofuran, 1:1) and recrystallized from ethanol to obtain the title compound (0.22 g, yield 18%).

Provenance & Evidence