反应详情

A mixture of 3-dimethylamino-1-(2-chloro-4-pyridyl)-2-propen-1-one (1.05 g, 5.0 mmol), 3-ethoxycarbonylmethyl-phenyl-guanidine nitrite (1.42 g, 5.0 mmol), lithium hydroxide (0.12 g, 5.0 mmol) in 2-butanol (15 mL) is heated to reflux for 24 hours. After cooling to room temperature, the solvent is evaporated under reduced pressure. Water (40 mL) is added and extracted with ethyl acetate (2×50 mL). The combined organic layers are dried over sodium sulfate, filtrated and concentrated. The residue is dissolved in ethanol (30 mL) and treated with lithium hydroxide (0.48 g, 20 mmol). The reaction mixture is heated to reflux for 1 hour. After cooling to room temperature, the mixture is concentrated. The residue is dissolved in water and acidified with 10% hydrochloric acid. The solid is collected by filtration and washed with water, methanol and dried to give N-[3-carboxymethyl-phenyl]-4-(2-chloro-4-pyridyl)-2-pyrimidineamine (1.34 g); ESI-MS (m/z): 341.0 (M++H).

1. temperatureis heated
2. temperatureto reflux for 24 hours
3. customthe solvent is evaporated under reduced pressure
4. additionWater (40 mL) is added
5. extractionextracted with ethyl acetate (2×50 mL)
6. dry with materialThe combined organic layers are dried over sodium sulfate
7. filtrationfiltrated
8. concentrationconcentrated
9. dissolutionThe residue is dissolved in ethanol (30 mL)
10. temperatureThe reaction mixture is heated
11. temperatureto reflux for 1 hour
12. temperatureAfter cooling to room temperature
13. concentrationthe mixture is concentrated
14. dissolutionThe residue is dissolved in water
15. filtrationThe solid is collected by filtration
16. washwashed with water, methanol
17. customdried