(Diethylamino)sulfur trifluoride → HCID 178526820, compound

Participants

Reaction Steps

To a solution of 1-(trans-4-{[(5-nitro-2-{[2-(trifluoromethoxy)benzyl]amino}pyrimidin-4-yl)amino]methyl}cyclohexyl)azetidin-3-ol (100 mg, 0.20 mmol) in CH2Cl2 (25 mL) was added dropwise a solution of diethylaminosulfur trifluoride (32 μL, 0.24 mmol) in CH2Cl2 (0.5 mL) at room temperature over a period of 15 min. When the reaction was complete, the mixture was treated with saturated NaHCO3 and stirred for 5 min. The organic phase was separated and washed with water. The organic phase was dried over Na2SO4 and concentrated. The resulting residue was purified by silica gel prep TLC using 95:5 CH2Cl2:MeOH as eluent to afford 26 mg of the title compound as a pale yellow solid (26%), m/z 499.1 [M+1]+.

Provenance & Evidence