反应详情

温度

100 °C

To a stirred solution of (iv) (50 mg, 0.212 mmol) in EtOH (750 mL) was added 5-methylpyridin-2-amine (25 mg, 0.23 mmol) and the resultant solution stirred at RT for 2 d, after which time a solid precipitated from solution. Triphenylphosphine (167 mg, 0.64 mmol) was added in a single portion and the reaction then heated at 100° C. in a sealed tube for 4 h. Upon cooling to RT, the reaction mixture was diluted with DCM (2 mL) and the organics were washed with aq. 30% hydrogen peroxide solution (2 mL). The organics were separated and filtered through a plug of MgSO4 and then purified by automated column chromatography (Biotage SP4, Grace 4 g silica cartridge) eluting with EtOAc:n-heptane (gradient elution, 0% equil. (2 CV), 0% (1CV), 0 to 100% (35 CV), 100% (5 CV)) to give (v) (27 mg, 43%). ESI-MS: calculated [M+H]+ 295.1, observed [M+H]+ 295.2.

1. customafter which time a solid precipitated from solution
2. customthe reaction
3. temperatureUpon cooling to RT
4. washthe organics were washed with aq. 30% hydrogen peroxide solution (2 mL)
5. customThe organics were separated
6. filtrationfiltered through a plug of MgSO4
7. custompurified by automated column chromatography (Biotage SP4, Grace 4 g silica cartridge)
8. washeluting with EtOAc