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To a solution of 2-bromo-4-methyl-pyridine (2.58g, 15 [MMOL)] in anhydrous THF (50 [ML) AT-30°C,] was added dropwise [NAHMDS] (solution 2M in THF, 15ml, 30 [MMOL)] and the mixture was stirred [AT-30°C] for 2 hours. A solution of intermediate 20 (2.74g, 15 [MMOL)] in THF (50 ml) was added dropwise and the mixture was stirred at -30°C for 1 hour and then poured into water. After extraction with EtOAc, the organic phase was dried over [NA2SO4] and concentrated under reduced pressure. The residue was purified by chromatography on silica gel [(CH2CI2/MEOH,] 99: 1). The title compound was obtained as a yellow solid (1.6g, 36percent); [[APCI] MS] m/z=295 (MH+).
2-(N-(tetrahydro-2H-pyran-4-yl)amino)-4-methylpyridine[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
0.11 g (49%)
tris-(dibenzylideneacetone)dipalladium(0); In hexane; ethyl acetate; toluene;
4-Methyl-N-(tetrahydro-2H-pyran-4-yl)pyridin-2-amine Example 3d Compound 3d was prepared according to general procedure B from 2-bromo-4-methylpyridine (0.20 g, 1.2 mmol), <strong>[33024-60-1]tetrahydro-2H-pyran-4-amine hydrochloride</strong> (0.19 g, 1.4 mmol), NaOt-Bu (0.27 g, 2.8 mmol), Pd2(dba)3 (21 mg, 0.023 mmol), BINAP (29 mg, 0.046 mmol), and toluene (30 mL) within 2 h at 70° C. flash chromatography: SiO2, from n-hexane/EtOAc 1:1 to 100percent EtOAc yield: 0.11 g (49percent)
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