Tetrabutylammonium Fluoride → 4-[3-(4-amino-[1,3,5]triazin-2-yl)-2-methyl-3H-benzoimidazol-5-yl]-2,2-dimethyl-but-3-yn-1-ol

Participants

Reaction Steps

In a solution of 4-{6-[4-(tert-butyl-dimethyl-silanyloxy)-3,3-dimethyl-but-1-ynyl]2-methyl-benzoimidazol-1-yl}-[1,3,5]triazin-2-ylamine (140 mg, 0.32 mmol) in THF (10 ml) was added tetrabutyl-ammonium fluoride (170 mg, 0.64 mmol). Then the solution stirred overnight at room temperature. The reaction mixture was washed with water and purified by column to afford the title compound 4-[3-(4-amino-[1,3,5]triazin-2-yl)-2-methyl-3H-benzoimidazol-5-yl]-2,2-dimethyl-but-3-yn-1-ol (5-e) (30 mg, 29%): 1H NMR (400 MHz, DMSO) delta 1.23 (s, 6H), 2.89 (s, 3H), 3.39 (d, J=6.0 Hz, 2H), 5.00 (t, J=5.6 Hz, 2H), 7.29 (dd, J=1.6, 8.4 Hz, 1H), 7.55 (d, J=8.4 Hz, 1H), 7.99 (s, 1H), 8.02 (s, 1H), 8.33 (t, J=0.4 Hz, 1H), 8.65 (s, 1H). LCMS m/z=+323.1 (M+H)+.

Provenance & Evidence