Acetylpyrazine → 4-[1-(4-amino-1,3,5-triazin-2-yl)-2-methyl-1H-1,3-benzodiazol-6-yl]-2-(pyrazin-2-yl)but-3-yn-2-ol

Participants

Reaction Steps

To a solution of 4-(6-ethynyl-2-methyl-1,3-benzodiazol-1-yl)-1,3,5-triazin-2-amine (80 mg, 0.29 mmol) in THF (0.5 mL) at −78° C. under N2 (g) was added 2M LDA in THF (0.43 mL, 0.86 mmol). After 5 min 1-pyrazin-2-yl-ethanone (105 mg, 0.86 mmol) in THF (0.5 mL) was added. After 20 min, the mixture was allowed to warm to RT and was stirred for 1 hr. The reaction mixture was quenched by addition of sat aq NH4Cl (0.5 mL). The volatiles were removed by evaporation under reduced pressure. The mixture was diluted with EtOAc (10 ml) and washed with water (2 mL), dried (Na2SO4), filtered and concentrated in vacuo. Purification by Biotage chromatography (100% DCM to 8% MeOH/DCM) gave the title compound (15 mg, 14% yield); 1H NMR (250 MHz, DMSO) delta 1.86 (3H, s), 2.89 (3H, s), 6.63 (1H, s), 7.32 (1H, dd, J=8.22, 1.52 Hz), 7.58 (1H, d, J=8.22 Hz), 7.96 (1H, s), 7.98 (1H, s), 8.39 (1H, d, J=1.22 Hz), 8.59-8.63 (1H, m), 8.63-8.67 (2 H, m), 9.02 (1H, d, J=1.37 Hz); LC-MS: m/z+373.4 (M+H)+.

Provenance & Evidence