تفاعل #2075729

معادلة التفاعل

HCl

Sodium methoxide

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

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

→

solid

المردود 8.0%

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

المردود 8.0%

المذيبات

MeOH

ظروف التفاعل

المعالجة

1. 1
   أخرىthe reaction
2. 2
   استخلاصThe reaction was extracted with ethyl acetate thrice
3. 3
   غسيلwashed with brine
4. 4
   أخرىdried
5. 5
   ترشيحfiltered
6. 6
   تركيزconcentrated
7. 7
   أخرىThe product was purified by flash chromatography on silica gel (0-50% EtOAc/hexane) the
8. 8
   أخرىrecrystallized from dichloromethane/hexane

الإجراء التجريبي

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).

المصدر