反应详情

1.0 g of 2,4-dimethyl-5-ethylaminomethylthiazole, 1.5 g of 2-chloro-3-nitro-6-methoxypyridine, 5.0 g of potassium carbonate, 20 mL of N,N-dimethylformamide (DMF) were added into a 150 mL of single-neck flask equipped with a magnetic stirrer. And the reaction mixture was stirred at room temperature overnight. And then extracted with ethyl acetate, the organic layer was separated while the aqueous layer was extracted with ethyl acetate twice. The organic phases were combined, and dried over anhydrous sodium sulfate after washed with an iced aqueous sodium chloride solution twice, then remove the solvent under reduced pressure to obtain 1.5 g of crude product which was purified by a silica gel column chromatography using a petroleum ether/ethyl acetate (20/1) as an eluent to obtain 0.49 g of 6-methoxy-N-(2,4-dimethylthiazole-5-yl)methyl)-N-ethyl-3-nitropyridine-2-amine, having the content of 98%, as a yellow viscous liquid, and solidified after standing. GC-MS (M+) (EI, 70 eV, m/z) calc: 322. found: 322. 1H NMR (CDCl3/TMS, 300 MHz) δ (ppm) 1.199 (t, J=7.2 Hz, 3H, CH3), 2.383 (s, 3H, CH3), 2.603 (s, 3H, CH3), 3.303 (q, J=7.2 Hz, 2H, CH2), 3.960 (s, 3H, CH3), 4.778 (s, 2H, CH3), 6.151 (d, J=8.7 Hz, 1H, Py H), 8.141 (d, J=9.0 Hz, 1H, Py H).

1. customequipped with a magnetic stirrer
2. extractionAnd then extracted with ethyl acetate
3. customthe organic layer was separated while the aqueous layer
4. extractionwas extracted with ethyl acetate twice
5. dry with materialdried over anhydrous sodium sulfate
6. washafter washed with an iced aqueous sodium chloride solution twice
7. customremove the solvent under reduced pressure
8. customto obtain 1.5 g of crude product which
9. customwas purified by a silica gel column chromatography