반응 #1583829

반응 방정식

methyl N-[[2-chloro-5-[3-(dimethylamino)-1-oxo-2-propen-1-yl]phenyl]-methyl]carbamate

product

methyl N-[[2-chloro-5-[3-(dimethylamino)-1-oxo-2-propen-1-yl]phenyl]methyl]carbamate

4-methylbenzamidine hydrochloride

sodium hydride

ammonium chloride

→

title compound

methyl N-[[2-chloro-5-[2-(4-methylphenyl)-4-pyrimidinyl]phenyl]methyl]-carbamate

용매

methanol

반응 조건

후처리

1. 1
   온도The reaction mixture was heated
2. 2
   온도at reflux overnight
3. 3
   농축the mixture was concentrated under reduced pressure
4. 4
   workup.DISSOLUTIONThe resulting residue was dissolved in ethyl acetate
5. 5
   세척washed with saturated aqueous sodium carbonate
6. 6
   건조dried over magnesium sulfate
7. 7
   여과filtered
8. 8
   농축concentrated under reduced pressure
9. 9
   기타The resulting residue was purified by medium pressure liquid chromatography (0 to 100% gradient of ethyl acetate in hexanes as eluant)

실험 절차

To mixture of methyl N-[[2-chloro-5-[3-(dimethylamino)-1-oxo-2-propen-1-yl]phenyl]-methyl]carbamate (i.e. the product of Step A, Example 4) (0.43 g, 1.44 mmol), 4-methylbenzamidine hydrochloride (0.74 g, 4.33 mmol) and sodium hydride (0.14 g, 5.8 mmol) at 0° C. was slowly added methanol (5 mL). The reaction mixture was heated at reflux overnight. A solution of saturated ammonium chloride was added to the reaction mixture, and the mixture was concentrated under reduced pressure. The resulting residue was dissolved in ethyl acetate, washed with saturated aqueous sodium carbonate, dried over magnesium sulfate, filtered and concentrated under reduced pressure. The resulting residue was purified by medium pressure liquid chromatography (0 to 100% gradient of ethyl acetate in hexanes as eluant) to provide the title compound, a compound of the present invention, as a solid (0.160 g).

출처