Water → 1-(6-Amino-pyridin-2-yl)-pentan-2-one

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Reaction Conditions

Reaction Steps

1,1,1,3,3,3-Hexamethyl-2-(6-methyl-pyridin-2-yl)-disilazane (1 g, Engelhardt, J. Chem. Soc. Chem. Commun.,1990, 89) under an argon atmosphere in THF (20 mL) was cooled to −20° C. and treated dropwise at −20° C. with 4.95 mL of a 1.6 M solution of N-butyllithium in hexane over a period of 1 h. The solution was stirred 1 h at −20° C., N-butyronitrile (0.301 g) was added and the mixture was allowed to warm to RT. It was then treated with 1.25 N HCL in methanol (6.34 ml) and stirred for 30 minutes at RT. The mixture was poured into water (pH 1) and extracted with AcOEt that was discarded, the water layer was brought to pH 8 with solid KHCO3 and extracted twice with AcOEt. The layers were separated, the organic layer dried over Na2SO4, filtered and evaporated to give 1-(6-Amino-pyridin-2-yl)-pentan-2-one as viscous yellow oil (0.34 g) that was used without further purification in the next step. MS (EI): 179.2 (M+).

Provenance & Evidence