Reaktion #937128

Reaktionsgleichung

propargyl bromide

3-(2,4-dichloro-5-ethoxycarbonylaminophenyl)-1-methyl-6-trifluoromethyl-2-oxo-1,2-dihydropyrazine

compound 1-346

3-(2,4-dichloro-5-ethoxycarbonylaminophenyl)-1-methyl-6-trifluoromethyl-2-oxo-1,2-dihydropyrazine

ammonium chloride

sodium hydride

→

3-{2,4-dichloro-5-[N-(ethoxycarbonyl)propargylamino]phenyl}-1-methyl-6-trifluoromethyl-2-oxo-1,2-dihydropyrazine

Ausbeute 16.0%

Lösungsmittel

tetrahydrofuran

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGthe mixture was stirred at 0° C. for 1 hour
2. 2
   SonstigeAfter completion of the reaction
3. 3
   Extraktionfollowed by extraction with diethyl ether
4. 4
   TrocknenThe organic layer was dried with anhydrous magnesium sulfate
5. 5
   Einengenconcentrated

Vorschrift

Then, a mixture of 20 mg of sodium hydride (60% in oil) and 1.3 ml of tetrahydrofuran was cooled to 0° C. To this was added dropwise a solution of 0.21 g of 3-(2,4-dichloro-5-ethoxycarbonylaminophenyl)-1-methyl-6-trifluoromethyl-2-oxo-1,2-dihydropyrazine (present compound 1-346) in 1.3 ml of tetrahydrofuran. After stirring at 0° C. for 10 minutes, 42 μl of propargyl bromide was added, and the mixture was stirred at 0° C. for 1 hour. After completion of the reaction, the reaction mixture was poured into saturated ammonium chloride solution, followed by extraction with diethyl ether. The organic layer was dried with anhydrous magnesium sulfate and concentrated. The residue was subjected to silica gel column chromatography, which afforded 36 mg (yield, 16%) of 3-{2,4-dichloro-5-[N-(ethoxycarbonyl)propargylamino]phenyl}-1-methyl-6-trifluoromethyl-2-oxo-1,2-dihydropyrazine (present compound 1-351; m.p., 132.3° C.).

Quelle