反应详情

温度

100 °C

A mixture of 3.42 g (9.9 mmol) of 4-(1-(but-3-enyl)hydrazinyl)-2-chloro-N-(2,6-dimethylphenyl)pyrimidine-5-carboxamide 31 (Example 1, Step C) in 100 mL of toluene was treated with 2.16 g (95%, 9.9 mmol) of phosphorus pentachloride. The resulting orange slurry was heated at 100° C. for 1.75 h, and then was concentrated. The residue was dissolved in CH2Cl2 (250 mL) and washed with saturated aqueous sodium bicarbonate (150 mL). The aqueous layer was extracted with more CH2Cl2 (100 mL). The combined organic layers were dried over Na2SO4, filtered, and the filtrate was purified by chromatography on silica gel (hexanes:EtOAc, 4:1) to give the title compound 32. 1H-NMR (CDCl3) δ 2.24 (s, 6H), 2.62-2.68 (m, 2H), 4.31 (t, J=7.2 Hz, 2H), 4.99 (dd, J=10.2 Hz, 1.6 Hz, 1H), 5.05 (dd, J=17.1 Hz, 1.6 Hz, 1H), 5.72-5.83 (m, 1H), 6.06 (s, 1H), 7.13-7.22 (m, 3H), 7.58 (s, 1H). Mass Spectrum (ESI) m/e=328.1 (M+1).

1. concentrationwas concentrated
2. dissolutionThe residue was dissolved in CH2Cl2 (250 mL)
3. washwashed with saturated aqueous sodium bicarbonate (150 mL)
4. extractionThe aqueous layer was extracted with more CH2Cl2 (100 mL)
5. dry with materialThe combined organic layers were dried over Na2SO4
6. filtrationfiltered
7. customthe filtrate was purified by chromatography on silica gel (hexanes:EtOAc, 4:1)