Trimethylsilyl iodide → HCID 178518776, compound

Participants

Reaction Steps

Trimethylsilyliodide (0.80 mL, 5.6 mmol) was added under N2 to a suspension of trans-4-[4-(3-methoxyindazol-1-yl)-pyrimidin-2-ylamino]-cyclohexanol (251 mg, 0.7 mmol) in chloroform (10 mL). The reaction mixture immediately became homogeneous, but within 1 hour a suspension formed, and the resulting mixture was stirred for 3 days. An additional aliquot of trimethylsilyliodide (2 mL, 14 mmol) was added, and the resulting mixture was heated to reflux overnight and stirred at RT for one day. The reaction mixture was then poured onto ice water and extracted with DCM. The insoluble solids were filtered and dissolved in a mixture of MeOH and DCM, the combined organic layers dried over Na2SO4, filtered and concentrated under reduced pressure onto silica gel. The residue was purified by flash chromatography (MeOH/DCM, gradient from 3:97 to 5:95) to give trans-1-[2-(4-hydroxycyclohexylamino)-pyrimidin-4-yl]-1,2-dihydroindazol-3-one (71 mg, 30% yield) as an off-white solid. MS=326 [M+H]+; MP=263.5-264.4° C.

Provenance & Evidence