반응 #2075729

반응 방정식

HCl

Sodium methoxide

2-ethoxy-3-oxo-succinic acid diethyl ester

4-chloro-2-fluoro-3-methoxybenzamidine hydrochloride

→

solid

수율 8.0%

2-(4-Chloro-2-fluoro-3-methoxyphenyl)-5-ethoxy-6-hydroxypyrimidine-4-carboxylic acid methyl ester

수율 8.0%

용매

MeOH

반응 조건

후처리

1. 1
   기타the reaction
2. 2
   추출The reaction was extracted with ethyl acetate thrice
3. 3
   세척washed with brine
4. 4
   기타dried
5. 5
   여과filtered
6. 6
   농축concentrated
7. 7
   기타The product was purified by flash chromatography on silica gel (0-50% EtOAc/hexane) the
8. 8
   기타recrystallized from dichloromethane/hexane

실험 절차

Sodium methoxide (12 mL, 62.74 mmol) was added dropwise to a solution of 2-ethoxy-3-oxo-succinic acid diethyl ester (9.7 g of 75% purity, 31.37 mol), 4-chloro-2-fluoro-3-methoxybenzamidine hydrochloride (5 g, 20.91 mol) and MeOH (24 mL). The reaction was allowed to stir for 1 hour. The reaction was cooled to 0° C. and 1 N HCl was added to acidify the reaction. The reaction was extracted with ethyl acetate thrice. The organic extracts were combined, washed with brine, dried, filtered and concentrated. The product was purified by flash chromatography on silica gel (0-50% EtOAc/hexane) the recrystallized from dichloromethane/hexane to give a white solid (623mg, 8% yield): mp 173-175° C.: 1H NMR (CDCl3) δ 11.28 (br s, 1H), 7.78 (dd, 1H), 7.31 (dd, 1H), 4.35 (q, 2H), 4.02 (s, 3H), 3.98 (s, 3H), 1.38 (t, 3H).

출처