Ammonium Chloride → HCID 24823963, compound

Participants

Reaction Steps

To a solution of 4-(4-benzotriazol-1-yl-pyrimidin-2-ylamino)-cyclohexanone (764 mg, 2.5 mmol) in 80 mL of THF, cooled at −78° C., was added dropwise methylmagnesium chloride (3.5 mL, 3.0 M in THF, 10.5 mmol). The reaction mixture immediately turned bright yellow in color; it was then allowed to warm to RT. The reaction did not reach completion, so it was re-cooled to −78° C. and an additional aliquot of MeMgCl (3 mL, 9 mmol) was added. The resulting mixture was warmed to RT and then poured onto an aqueous solution of NH4Cl; it was extracted with EtOAc. The organic layer was separated, dried over Na2SO4 and filtered; the solvent was evaporated under reduced pressure. The crude residue was purified by column chromatography (1-5/99-95 MeOH/CH2Cl2) to give: a less polar trans-isomer (130 mg, 16% yield, mp=193.0-195.4° C.; MS=325 (M+H)+), and the more polar cis-isomer (360 mg, 45% yield, mp=202.1-205.6° C.; MS=325 (M+H)+) as white crystalline solids.

Provenance & Evidence