反应详情

温度

-10 °C

To a solution of cyanuric chloride (3.69 g, 20 mmol) in DCM (100 mL) at −10° C. was added methylmagnesium bromide (20 mL, 60 mmol, 3.0M solution in ether) maintaining the temperature at −10° C. The reaction was stirred for 4 h at −10° C. and then quenched with saturated ammonium chloride solution (20 mL). The organic layer was separated, dried (MgSO4) and filtered. The filtrate was cooled to 0° C. before the addition of 4-methoxybenzylamine (2.74 g, 20 mmol) and DIPEA (2.6 g, 20 mmol) took place. The reaction was stirred for 18 h at r.t. The organic layer was washed with water (2×20 mL), separated, dried (MgSO4), filtered and the solvent removed in vacuo. The residue was crystallised from diisopropyl ether affording the title compound as a pale yellow solid (2.8 g, 51%). δH (CDCl3) 7.23 (d, J 9.2 Hz, 2H), 6.85 (d, J 9.2 Hz, 2H), 5.62 (br s, 1H), 4.56 (d, J 8.1 Hz, 2H), 3.79 (s, 3H), 2.38 (s, 3H). LCMS (ES+) 265 (M+H)+, RT 2.80 minutes (Method 5).

1. customquenched with saturated ammonium chloride solution (20 mL)
2. customThe organic layer was separated
3. dry with materialdried (MgSO4)
4. filtrationfiltered
5. stirringThe reaction was stirred for 18 h at r.t
6. washThe organic layer was washed with water (2×20 mL)
7. customseparated
8. dry with materialdried (MgSO4)
9. filtrationfiltered
10. customthe solvent removed in vacuo
11. customThe residue was crystallised from diisopropyl ether affording the title compound as a pale yellow solid (2.8 g, 51%)
12. customLCMS (ES+) 265 (M+H)+, RT 2.80 minutes (Method 5)