Reaktion #1246855

Reaktionsgleichung

2-(4-nitrophenyl)ethanimidamide hydrochloride

dimethyl acetyl-succinate

sodium methoxide

thionyl chloride

→

methyl [4-hydroxy-6-methyl-2-(4-nitrobenzyl)-pyrimidin-5-yl]acetate

Ausbeute 38.0%

Lösungsmittel

Acetone

MeOH

MeOH

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturwas refluxed for 15 hours
2. 2
   Sonstigethe separated solids were collected by suction
3. 3
   TemperaturThe resulting mixture was refluxed for 16 hours
4. 4
   Temperaturcooled to room temperature
5. 5
   Sonstigethe precipitated solids were collected by suction
6. 6
   Waschenrinsed with acetone
7. 7
   Sonstigedried under high vacuum for 4 hours

Vorschrift

A mixture of 2-(4-nitrophenyl)ethanimidamide hydrochloride (0.22 g, 1.0 mmol), dimethyl acetyl-succinate (0.19 g, 1.0 mmol), and sodium methoxide (0.07 g, 1.3 mmol) in MeOH (10 mL) was refluxed for 15 hours. After cooling to room temperature, the separated solids were collected by suction and added to a pre-formed solution of thionyl chloride (0.65 mL, 8.9 mmol) in MeOH (7.5 mL). The resulting mixture was refluxed for 16 hours and then cooled to room temperature. Acetone was added and the precipitated solids were collected by suction, rinsed with acetone and dried under high vacuum for 4 hours to give methyl [4-hydroxy-6-methyl-2-(4-nitrobenzyl)-pyrimidin-5-yl]acetate (0.12 g, 38% yield) as a white solid.

Quelle