Potassium bis(trimethylsilyl)amide → HCID 178518575, compound

Participants

Reaction Steps

To a cold (−78° C.), stirred solution of N-[3-benzenesulfinylmethyl-5-(2-fluorophenyl)-3H-1,2,3-triazol-4-yl]-2-chloro-2-phenylacetamide (850 mg, 1.81 mmol) in dry tetrahydrofuran (50 ml) was added a solution of potassium bis(trimethylsilyl)amide (8.44 ml, 0.752 M in toluene, 6.34 mmol) and the reaction stirred for 90 minutes. The reaction was then transferred to a −20° C. bath and stirred for 15 minutes. The reaction was quenched by pouring into water (200 ml) and stirring for 10 minutes. The aqueous mixture was acidified with citric acid (10% aqueous) and extracted with ethyl acetate (2×200 ml). The combined organic extracts were washed with water (100 ml), brine (100 ml), dried (Na2SO4) and concentrated iin vacuo to about 10 ml total volume. 3-(2-Fluorophenyl)-6-phenyl-4H-1,2,3-triazolo[1,5-α]pyrimidin-5-one (355 mg, 64%) thus obtained was collected by filtration and washed with diethyl ether. The title product was used in subsequent reactions without further purification. δH (400 MHz, DMSO) 7.32-7.39 (6H, m, ArH, 7.70-7.74 (3H, m, ArH), 9.17 (1H, s, PhC═CH), 12.70 (1H, br s, NH); m/z (ES+) 307 (M+H+).

Provenance & Evidence