Tetrabutylammonium Fluoride → HCID 58346552, compound

Participants

Reaction Steps

To 80 mL THF cooled to 0° C. was added 2-(2-{[tert-butyl(dimethyl)silyl]oxy}ethyl)-N-[3-chloro-4-(pyridin-2-ylmethoxy)phenyl]-4,5-dihydro-2H-pyrimido[5′,4′:4,5]thieno[2,3-e]indazol-6-amine (2.40 g, 3.9 mmol). To the homogeneous mixture was then added TBAF in THF (1M, 4.3 mL). The dark contents were then stirred with warming to rt over a 1 h period, after which time the solvent was removed under reduced pressure. The crude residue was diluted with water (100 mL) and vigorously stirred. The precipitate formed was collected by filtration and further triturated with ethanol to afford the desired product (1.90 g, 92%) as a light-brown solid. 1H-NMR (DMSO-d6) δ 8.60 (d, 1H), 8.43 (s, 1H), 8.36 (s, 1H), 7.94 (s, 1H), 7.88 (td, 1H), 7.78 (d, 1H), 7.60 (d, 1H), 7.54 (dd, 1H), 7.38 (t, 1H), 7.24 (d, 1H), 5.29 (s, 2H), 4.94 (t, 1H), 4.12 (t, 2H), 3.74 (q, 2H), 3.39 (t, 2H), 2.93 (t, 2H); LCMS RT=2.32 min; [M+H]+=505.3.

Provenance & Evidence