1-(Bromomethyl)-2-(trifluoromethyl)benzene → HCID 66780526, compound

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Reaction Steps

Lithium bis(trimethylsilyl)amide (0.755 mL, 0.755 mmol) was added to a suspension of 2-(4-morpholinyl)[1,3]thiazolo[4,5-d]pyrimidin-7(4H)-one (90 mg, 0.378 mmol) in tetrahydrofuran (THF) (3 mL) at 0° C. under nitrogen. The mixture was stirred at 0° C. for 30 min before the addition of 1-(bromomethyl)-2-(trifluoromethyl)benzene (0.069 mL, 0.453 mmol). The mixture was warmed up to RT and stirred overnight. The solvent was removed and the residue was partitioned between DCM and brine. The organic layer was concentrated and the residue was purified on a biotage column (5% MeOH/DCM) to give 80 mg (55%) of the product (the undesired regioisomer (24 mg, 17%) was less polar on silica gel). LCMS (ES) m/z=397.0 (M+H)+, 1H NMR (400 MHz, CDCl3-d1) δppm 8.05 (s, 1H), 7.76 (d, J=7.6 Hz, 1H), 7.45˜7.55 (m, 2H), 7.05 (d, J=7.6 Hz, 1H), 5.54 (s, 2H), 3.80 (m, 4H), 3.58 (m, 4H).

Provenance & Evidence