Reaktion #959251

Reaktionsgleichung

Sodium methoxide

acetamidine hydrochloride

methyl 2-chloro-3-oxobutanoate

HCl

→

title compound

5-chloro-2,6-dimethylpyrimidin-4-ol

Lösungsmittel

MeOH

Et2O

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturcooled to room temperature
2. 2
   Einengenconcentrated in vacuo
3. 3
   workup.STIRRINGstirred vigorously for 10 mins
4. 4
   Filtrationthe solids collected by filtration

Vorschrift

Sodium methoxide (328 mg, 6.08 mmol, 30% solution in MeOH) was added to a stirring suspension of acetamidine hydrochloride (191 mg, 2.03 mmol) and methyl 2-chloro-3-oxobutanoate (500 mg, 3.04 mmol) in MeOH (10.1 mL). The reaction mixture was heated to 80° C. for 3 hours and then cooled to room temperature. With stirring, the reaction was treated with 2N HCl in Et2O (50 mL), and then concentrated in vacuo. The resulting solid was suspended in 1:1 acetone/CH2Cl2, stirred vigorously for 10 mins, and the solids collected by filtration to afford the title compound as a light yellow solid. The isolated product was sufficiently pure to use in the subsequent step without further purification. LRMS m/z (M+H) 159.2 found, 159.0 required.

Quelle