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N-(3,5-Dimethoxyphenyl)-5-phenyl-1,3-oxazol-2-amine[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
at 70℃; for 3h;
N-(3.5-Dimethoxyphenyl)-5-phenyl-1.3-oxazol-2-amine (5-3); A mixture of <strong>[62124-43-0]2-chloro-5-phenyl-1,3-oxazole</strong> (5-1, 0.050 g, 0.28 mmol) and 3,5-dimethoxyaniline (2-1, 0.213 g, 1.39 mmol) was heated to 70° C. After 3 hours the reaction was cooled and diluted with dimethylsulfoxide. The resulting solution was purified sequentially by reverse phase preparative HPLC and flash column chromatography (eluting with 82:18 hexanes/ethyl acetate) to afford pure 5-2. 1H NMR (CDCl3) delta 7.54 (d, 2H, J=7.0 Hz), 7.39 (t, 2H, J=7.3 Hz), 7.29-7.25 (m, overlapping with CHCl3), 7.16 (s overlapping with bs, 2H), 6.74 (d, 2H, J=2.1 Hz), 6.19 (tm 1H, J=2.2 Hz), 3.83 (s, 6H). MS [M+H]+=297.1. mp=173° C.
A solution of <strong>[42860-10-6]3-bromo-4-chlorobenzoic acid</strong> (250 mg, 1.1 mmol) in DMF (2 mL) was treated with PyBop (550 mg, 1.1 mmol) and DIPEA (370 uL, 2.1 mmol). After stirring the reaction mixture for5 min. 3,5-dimethoxy analine (105 mg, 0.69 mmol) was added and the reaction was stirred for 16 h. The reaction mixture was diluted with ethyl acetate and washed with 0.1 N HCl, 0.1 N sodium hydroxide and Brine, successively. The organic layer was dried (MgSO4) and concentrated, and crude 3-bromo-4-chloro-N-(3,5-dimethoxyphenyl)benzamide was used without further purification.
A solution of <strong>[42860-10-6]3-bromo-4-chlorobenzoic acid</strong> (250 mg, 1.1 mmol) in DMF (2 mL) was treated with PyBop (550 mg, 1.1 mmol) and DIPEA (370 uL, 2.1 mmol). After stirring the reaction mixture for 5 min. 3,5-dimethoxy analine (105 mg, 0.69 mmol) was added and the reaction was stirred for 16 h. The reaction mixture was diluted with ethyl acetate and washed with 0.1 N HCl, 0.1 N sodium hydroxide and Brine, successively. The organic layer was dried (MgSO4) and concentrated, and crude 3-bromo-4-chloro-N-(3,5-dimethoxyphenyl)benzamide was used without further purification.
3,5-dimethoxyaniline (59.9 g; 0.39 mol) was heated at 100C (melting) and 2-chloro-5- nitropyrimidin-4-amine (CAS 1920-66-7) (13.65 g; 78.20 mmol) was added rapidly. The heating was continued for 10 minutes. The reaction mixture was cooled to room temperature and poured onto DCM and saturated NaHC03 solution. The insoluble material was filtered, washed with water, DCM/MeOH, then Et20 and dried, yielding 20.2 g (88%) of intermediate 4. This intermediate was used as it is for the next step. 1H NMR (500 MHz, DMSO-d6) delta 9.66 - 10.49 (m, 1 H), 8.97 (s, 1 H), 8.04 - 8.69 (m, 2H), 7.09 (s, 2H), 6.21 (s, 1 H), 3.74 (s, 6H); MS (ESI+) m/z (%) (r.t. 5.66) 292 ( 00) [M+H]+
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