Tetrabutylammonium Fluoride → 4-[6-ethynyl-2-(oxetan-3-yloxy)-1H-1,3-benzodiazol-1-yl]pyrimidin-2-amine

Participants

Reaction Steps

To a solution of 4-[2-(oxetan-3-yloxy)-6-[2-(trimethylsilyl)ethynyl]-1H-1,3-benzodiazol-1-yl]pyrimidin-2-amine (450 mg, 1.19 mmol) in dry THF (5 mL) at RT was introduced TBAF (0.88 mL of a 1M solution in THF, 0.88 mmol). After 20 minutes, the reaction mixture was concentrated in vacuo, DCM (5 mL) added and the solution re-evaporated to dryness in vacuo (re-evaporation process repeated twice). Purification of the residue by silica gel flash column chromatography (eluent: DCM containing a 2-10% gradient of methanol) furnished the title compound as a yellow solid: 1H (500 MHz, DMSO) delta 4.83-4.70 (2H, m), 5.04-4.93 (2H, m), 5.85-5.77 (1H, m), 7.18-7.07 (3H, m), 7.33 (1H, dd, J=8.2, 1.5 Hz), 7.45 (1H, d, J=8.2 Hz), 8.36 (1H, s), 8.40 (1H, d, J=5.5 Hz); LCMS: m/z=+307.95 (M+H)+.

Provenance & Evidence