Boron tribromide → 4-[2-(5,8-Difluoroquinazolin-4-ylamino)-ethyl]-2-methylphenol

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Reaction Steps

To a solution of (5,8-difluoroquinazolin-4-yl)-[2-(4-methoxy-3-methylphenyl)-ethyl]-amine (0.86 g, 2.6 mmol) in CH2Cl2 (10 mL) cooled to −50° C., was added 7.8 mL BBr3 (1 M in CH2Cl2, 7.8 mmol). The solution was allowed to warm to room temperature and stirred overnight, and then quenched slowly with methanol. The solvent was removed by rotary evaporation, and the residue was diluted with water and stirred for a few min. The pale yellow solid precipitate was collected by suction filtration, washed with water, and dried in vacuum at 50° C. overnight to give 0.83 g (quantitative yield) of 4-[2-(5,8-difluoroquinazolin-4-ylamino)-ethyl]-2-methylphenol. 1H NMR (d4-DMSO+d6-acetone): δ 9.5-8.5 (m, 3H), 7.97 (m, 1H), 7.61 (m, 1H), 6.99 (s, 1H), 6.91 (d, J=8.1 Hz, 1H), 6.75 (d, J=8.1 Hz, 1H), 3.92 (m, 2H), 2.88 (t, J=7.8 Hz, 2H), 2.11 (s, 3H). LC/MS: 316.04 (M++1). The product was used in the following reaction without further purification. M.P. 244-251° C.

Provenance & Evidence