Ammonium Chloride → 4-[1-(2-aminopyrimidin-4-yl)-2-ethoxy-1H-1,3-benzodiazol-6-yl]-2-(pyrimidin-2-yl)but-3-yn-2-ol

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-(2-ethoxy-6-ethynyl-1H-1,3-benzodiazol-1-yl)pyrimidin-2-amine (110 mg, 0.37 mmol) in dry THF (1 mL) at −78° C. was introduced lithium diisopropylamide (0.47 mL of a 2M solution in THF, 0.935 mmol). After 5 minutes, 1-pyrimidin-2-yl-ethanone (81 mg, 0.65 mmol) was added and the reaction mixture maintained at −78° C. for 20 minutes. Following 30 minutes at RT, saturated aqueous ammonium chloride (0.5 ml) was added and the solution concentrated in vacuo. The residue was dissolved in DCM (10 mL), washed with water (2 mL), dried (Na2SO4), filtered and concentrated in vacuo. Purification of the residue by column chromatography (Biotage, DCM containing a 0-8% gradient of methanol) furnished the title compound as a beige solid: 1H NMR (500 MHz, DMSO) delta 1.44 (3H, t, J=7.09 Hz), 1.88 (3H, s), 4.63 (2H, q, J=7.09 Hz), 6.14 (1H, s), 6.96 (1H, d, J=5.36 Hz), 7.09 (2H, br.s.), 7.22 (1H, dd, J=8.20, 1.58 Hz), 7.43 (1H, d, J=8.20 Hz), 7.49 (1H, t, J=4.81 Hz), 8.10 (1H, d, J=1.10 Hz), 8.38 (1H, d, J=5.36 Hz), 8.88 (2H, d, J=4.89 Hz); LC-MS: m/z=+402.45 (M+H)+.

Provenance & Evidence