反应详情

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+).

1. customwas then transferred to a −20° C.
2. stirringstirred for 15 minutes
3. customThe reaction was quenched
4. additionby pouring into water (200 ml)
5. stirringstirring for 10 minutes
6. extractionextracted with ethyl acetate (2×200 ml)
7. washThe combined organic extracts were washed with water (100 ml), brine (100 ml)
8. dry with materialdried (Na2SO4)
9. concentrationconcentrated iin vacuo to about 10 ml total volume