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With diethylazodicarboxylate; In tetrahydrofuran; hexane;
To a stirring, 0 C. solution of 3,5-dimethyl-4-hydroxybenzaldehyde (1.5018 g, 10 mmol), <strong>[146667-84-7]N-Boc-3-piperidineethanol</strong> (2.153 g, 10 mmol), and triphenylphosphene (2.964 g, 11.3 mmol) in 40 mL THF, was added dropwise over 10 min 1.78 mL (11.3 mmol) DEAD the mixture was mixed slowly and allowed to warm to ambient temperature and stirred for 12 hours. The mixture was concentrated in vacuo, and Hexane/DCM was added to precipitate out triphenylphosphene oxide, which was filtered off. The filtrate was concentrated in vacuo, and the residue was flash chromatographed on silica gel, the appropriate fractions combined to give the desired boc-amino ether.
tert-butyl 3-(2-(6-(2-chlorophenyl)-2-(methylthio)-7-oxopyrido[2,3-d]pyrimidin-8(7H)-yl)ethyl)piperidine-1-carboxylate[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
60%
With di-isopropyl azodicarboxylate; triphenylphosphine; In N,N-dimethyl-formamide; at 0 - 20℃;Inert atmosphere;
To a mixture of 6-(2-chlorophenyl)-2-(methylthio)pyrido [2, 3 -d]pyrimidin-7(8H)-one (3.03 g, 10 mmol, 1.0 equiv), <strong>[146667-84-7]tert-butyl 3-(2-hydroxyethyl)piperidine-1-carboxylate</strong> (2.52 g, 11 mmol, 1.1 equiv) and PPh3 (5.24 g, 20 mmol, 2.0 equiv) in DMF (30 mL) was added dropwise DIAD (4.04 g, 20 mmol, 2.0 equiv) at 00 C under N2. The mixture was stirred at rt overnight.The resulting mixture was poured into water and extracted with EtOAc, washed with water, dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was purified by column chromatography using PE/EtOAc (10/1 to 3/1). This resulted in 5.15 g (60%) of tert-butyl 3 -(2-(6-(2-chlorophenyl)-2-(methylthio)-7-oxopyrido [2,3 -d]pyrimidin-8(7H)- yl)ethyl)piperidine- 1 -carboxylate as a white solid.
60%
With di-isopropyl azodicarboxylate; triphenylphosphine; In N,N-dimethyl-formamide; at 0 - 20℃;Inert atmosphere;
To a mixture of 6-(2-chlorophenyl)-2-(methylthio)pyrido[2,3-d]pyrimidin-7(8H)-one (3.03 g, 10 mmol, 1.0 equiv), tert-butyl 3-(2-hydroxyethyl)piperidine-l-carboxylate (2.52 g, 11 mmol, 1.1 equiv) and PPh3 (5.24 g, 20 mmol, 2.0 equiv) in DMF (30 mL) at 0 0 C under N2 was added DIAD (4.04 g, 20 mmol, 2.0 equiv) dropwise. The mixture was stirred at rt overnight and then poured into water and extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous sodium sulfate, filtered and concentrated under vacuum. The residue was purified by column chromatography using petroleum ether/ethyl acetate (10/1 to 3/1) to give 5.15 g (60%) of tert-butyl 3-(2-(6-(2-chlorophenyl)-2-(methylthio)-7-oxopyrido[2,3- d]pyrimidin-8(7H)-yl)ethyl)piperidine-l-carboxylate as a white solid.
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