Tetrabutylammonium Fluoride → 4-(2-ethoxy-6-ethynyl-1H-1,3-benzodiazol-1-yl)pyrimidin-2-amine

Participants

Reaction Steps

To a solution of 4-{2-ethoxy-6-[2-(trimethylsilyl)ethynyl]-1H-1,3-benzodiazol-1-yl}pyrimidin-2-amine (170 mg, 0.48 mmol) in dry THF (5 mL) at RT was introduced TBAF (0.58 mL of a 1M solution in THF, 0.58 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 column chromatography (Biotage, DCM containing a 1-7% gradient of methanol) furnished the title compound as a beige solid: 1H NMR (500 MHz, DMSO) delta 1.46 (3H, t, J=7.01 Hz), 4.10 (1H, s), 4.61-4.68 (2H, m), 6.97-7.03 (1H, m), 7.09 (2H, br. s.), 7.33 (1H, dd, J=8.12, 1.34 Hz), 7.45 (1H, d, J=8.04 Hz), 8.33 (1H, s), 8.37 (1H, d, J=5.52 Hz); LC-MS: m/z=+280.00 (M+H)+.

Provenance & Evidence