(2-amino-5-bromo-3-chlorophenyl)methanol

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of (2-amino-5-bromo-3-chlorophenyl)methanol (10.0 g, 42.5 mmol) and manganese oxide (21.9 g, 255 mmol) in dichloromethane (400 mL) was stirred at room temperature overnight. The solid was filtered off, and the filtrate was concentrated to give the title compound as a light yellow solid (9.0 g, 91%), which was directly used in the next step without further purification. The solid was filtered off the filtrate was concentrated

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 2-amino-5-bromo-3-chlorobenzoic acid (13.0 g, 52.0 mmol) in THF (200 mL) was added borohydride in THF (300 mL, 1N) at ice/water bath, and the reaction mixture was stirred at room temperature overnight. The mixture was quenched with methanol (100 mL) and concentrated to a volume of 50 mL. The residue was diluted with aqueous sodium bicarbonate (400 mL) and extracted with ethyl acetate (200 mL×3). The organic layers were separated, combined, washed by brine (100 mL), dried over sodium sulfate, filtered and concentrated to afford the title product (10.0 g, 82%). MS (ES+) C7H7BrClNO requires: 234, 236, found: 236, 238 [M+H]+. The mixture was quenched with methanol (100 mL) concentrated to a volume of 50 mL The residue was diluted with aqueous sodium bicarbonate (400 mL) extracted with ethyl acetate (200 mL×3) The organic layers were separated washed by brine (100 mL) dried over sodium sulfate filtered concentrated

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of (2-amino-5-bromo-3-chlorophenyl)methanol (10.0 g, 42.5 mmol) and manganese oxide (21.9 g, 255 mmol) in dichloromethane (400 mL) was stirred at room temperature overnight. The solid was filtered off, and the filtrate was concentrated to give the title compound as a light yellow solid (9.0 g, 91%), which was directly used in the next step without further purification. The solid was filtered off the filtrate was concentrated

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 2-amino-5-bromo-3-chlorobenzoic acid (13.0 g, 52.0 mmol) in THF (200 mL) was added borohydride in THF (300 mL, 1N) at ice/water bath, and the reaction mixture was stirred at room temperature overnight. The mixture was quenched with methanol (100 mL) and concentrated to a volume of 50 mL. The residue was diluted with aqueous sodium bicarbonate (400 mL) and extracted with ethyl acetate (200 mL×3). The organic layers were separated, combined, washed by brine (100 mL), dried over sodium sulfate, filtered and concentrated to afford the title product (10.0 g, 82%). MS (ES+) C7H7BrClNO requires: 234, 236, found: 236, 238 [M+H]+. The mixture was quenched with methanol (100 mL) concentrated to a volume of 50 mL The residue was diluted with aqueous sodium bicarbonate (400 mL) extracted with ethyl acetate (200 mL×3) The organic layers were separated washed by brine (100 mL) dried over sodium sulfate filtered concentrated

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of (2-amino-5-bromo-3-chlorophenyl)methanol (10.0 g, 42.5 mmol) and manganese oxide (21.9 g, 255 mmol) in dichloromethane (400 mL) was stirred at room temperature overnight. The solid was filtered off, and the filtrate was concentrated to give the title compound as a light yellow solid (9.0 g, 91%), which was directly used in the next step without further purification. The solid was filtered off the filtrate was concentrated

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 2-amino-5-bromo-3-chlorobenzoic acid (13.0 g, 52.0 mmol) in THF (200 mL) was added borohydride in THF (300 mL, 1N) at ice/water bath, and the reaction mixture was stirred at room temperature overnight. The mixture was quenched with methanol (100 mL) and concentrated to a volume of 50 mL. The residue was diluted with aqueous sodium bicarbonate (400 mL) and extracted with ethyl acetate (200 mL×3). The organic layers were separated, combined, washed by brine (100 mL), dried over sodium sulfate, filtered and concentrated to afford the title product (10.0 g, 82%). MS (ES+) C7H7BrClNO requires: 234, 236, found: 236, 238 [M+H]+. The mixture was quenched with methanol (100 mL) concentrated to a volume of 50 mL The residue was diluted with aqueous sodium bicarbonate (400 mL) extracted with ethyl acetate (200 mL×3) The organic layers were separated washed by brine (100 mL) dried over sodium sulfate filtered concentrated

Conditions: temp:180.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of (2-amino-5-bromo-3-chlorophenyl)methanol (3.3 g, obtained from step 3) and urea (10.5 g, 15 equiv.) was heated to 180° C. with vigorous stirring for 1 hr. The reaction was cooled to room temperature and water was added. The solid was collected by filtration. Air-dried to give 2-hydroxyquinazoline as a yellow powder (2.18 g, crude). ES/MS m/z 259/261 (MH+). The reaction was cooled to room temperature The solid was collected by filtration Air-dried