[(1s,4s)-4-Aminocyclohexyl]methanol hydrochloride → (4-{4-[4-(3-Methanesulfonyl-propoxy)-indol-1-yl]-pyrimidin-2-ylamino}-cyclohexyl)-methanol

Participants

Reaction Steps

1-(2-Methanesulfinyl-pyrimidin-4-yl)-4-(3-methanesulfonyl-propoxy)-1H-indole (5.0 g, 13 mmol) and (4-amino-cyclohexyl)-methanol hydrochloride (2.46 g, 19 mmol) were heated at reflux in EtOH (100 mL) under N2 for 16 h. The reaction mixture was then cooled, the suspension filtered, the filtrate volume reduced by half, diluted with EtOAc and washed with water, dried over sodium sulfate, filtered and concentrated until precipitate formed. This suspension was filtered, and the filtrate concentrated again until precipitation, and the suspension filtered, and both precipitates were combined and solvent removed in vacuo to yield (4-{4-[4-(3-methanesulfonyl-propoxy)-indol-1-yl]-pyrimidin-2-ylamino}-cyclohexyl)-methanol (Compound 214, 2.93 g), as a light yellow powder.

Provenance & Evidence