Reaktion #424652

Reaktionsgleichung

n-butyllithium

n-hexane

ammonium chloride

Compound 98

N-[4-(2-Furyl)-5-(N-methoxy-N-methylcarbamoyl)thiazol-2-yl]pyridine-4-carboxamide

pyrimidine

2,2,6,6-Tetramethylpiperidine

→

Compound 375

Ausbeute 7.0%

N-[4-(2-Furyl)-5-(pyrimidin-4-ylcarbonyl)thiazol-2-yl]pyridine-4-carboxamide

Ausbeute 7.0%

Lösungsmittel

THF

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeat −78° C.
2. 2
   workup.STIRRINGby stirring at room temperature for 2 hours
3. 3
   Extraktionfollowed by extraction with ethyl acetate
4. 4
   WaschenThe organic layer was washed with a saturated aqueous solution of sodium chloride
5. 5
   Trocknendried over anhydrous magnesium sulfate
6. 6
   workup.DISTILLATIONthe solvent was distilled away under reduced pressure
7. 7
   SonstigeThe resulting residue was purified through silica gel column chromatography (ethyl acetate)

Vorschrift

2,2,6,6-Tetramethylpiperidine (0.233 mL, 1.38 mmol) was dissolved in THF (6 mL), and a 1.58 mol/L solution of n-butyllithium in n-hexane (0.880 mL, 1.38 mmol) was added thereto in a stream of argon at −78° C., followed by stirring at room temperature for 30 minutes. At −78° C., a solution of Compound 98 (150 mg, 0.419 mmol) and pyrimidine (0.0990 mL, 1.26 mmol) in THF (2 mL) was added to the reaction mixture, followed by stirring at room temperature for 2 hours. The reaction mixture was poured into a saturated aqueous solution of ammonium chloride, followed by extraction with ethyl acetate. The organic layer was washed with a saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate, and then the solvent was distilled away under reduced pressure. The resulting residue was purified through silica gel column chromatography (ethyl acetate) to afford the entitled Compound 375 (11.0 mg, 7%).

Quelle