Diisopropylethylamine → 2-(4-{4-[4-(3-Methanesulfonyl-propoxy)-indol-1-yl]-pyrimidin-2-ylamino}-cyclohexyl)-propan-2-ol

Participants

Reaction Conditions

Reaction Steps

1-(2-Methanesulfinyl-pyrimidin-4-yl)-4-(3-methanesulfonyl-propoxy)-1H-indole (538 mg, 1.4 mmol), 4-(2-hydroxyprop-2-yl)-cyclohexylammonium acetate (400 mg, 2 mmol), and DIEA (0.8 mL, 5 mmol) were combined in NMP (10 mL) and heated to 126° C. in a sealed tube for 4 h, cooled, and partitioned between water and EtOAc. The organic layer was separated and washed twice with water, dried over sodium sulfate, filtered and purified by flash chromatography (SiO2) with 3:97 MeOH/DCM, and recrystallized from MeOH/DCM, triturated with EtOAc and solvent evaporated to yield 2-(4-{4-[4-(3-methanesulfonyl-propoxy)-indol-1-yl]-pyrimidin-2-ylamino}-cyclohexyl)-propan-2-ol (Compound 166, 391 mg, 59%) as a white powder.

Provenance & Evidence