Aniline → 8-bromo-N-phenylquinazolin-2-amine

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LHMDS (1.0M in THF; 4.11 mL, 4.11 mmol) was added to a solution of 8-bromo-2-chloroquinazoline (Ark Pharm, Inc., Libertyville, Ill.; 500 mg, 2.053 mmol) and aniline (0.337 mL, 3.70 mmol) in THF (10 mL) at 0° C., and the resulting solution was stirred at 0° C. for 10 min. Saturated aq. NH4Cl (10 mL) was added, and the resulting mixture was partitioned between EtOAc (50 mL) and additional saturated aq. NH4Cl (30 mL). The organic layer was separated, washed with brine (30 mL), dried over Na2SO4, filtered and concentrated in vacuo. Chromatographic purification of the residue (silica gel, 0-10% MeOH/DCM) furnished 8-bromo-N-phenylquinazolin-2-amine (616 mg, 2.052 mmol, 100% yield) as a yellow solid: m/z (ESI, +ve) 300.0 (M+H)+.

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