Pyridine → 3-[bis(methylsulfanyl)methylene]-1-isopentyl-2,4(1H,3H)-pyridinedione

HRID 601420Notes

Reaction equation

[OH:1][C:2]1[CH:7]=[CH:6][N:5]([CH2:8][CH2:9][CH:10]([CH3:12])[CH3:11])[C:4](=[O:13])[CH:3]=1.N1C=CC=CC=1.S(OC)(O[C:24](SC)([S:27][CH3:28])[S:25][CH3:26])(=O)=O>O1CCOCC1>[CH3:26][S:25][C:24]([S:27][CH3:28])=[C:3]1[C:2](=[O:1])[CH:7]=[CH:6][N:5]([CH2:8][CH2:9][CH:10]([CH3:11])[CH3:12])[C:4]1=[O:13]

Participants

Conditions

Temperature: 90 °C

Procedure

The product of Example 457B (2.24 g, 12.37 mmol) in pyridine (8.0 mL, 98.96 mmol) and dioxane (50 mL) at 90° C. was treated with excess tris(methylthio)methyl methyl sulfate (prepared using the procedures in Synthesis, 22-25, 1988; M. Barbero, S. Cadamuro, I. Degani, R. Fochi, A. Gatti, V. Regondi), stirred at 90° C. for 1.5 hours and cooled to about 25° C. The reaction solution was decanted from the resulting solids and the solvent was removed under reduced pressure. The residue was dissolved in hexanes and loaded onto a pad of silica gel (300 mL) and eluted with hexane followed by dichloromethane then 25% ethyl acetate in dichloromethane to provide the title compound (2.42 g, 75%).

Workup

customprepared
customin Synthesis, 22-25, 1988
temperaturecooled to about 25° C
customThe reaction solution was decanted from the resulting solids
customthe solvent was removed under reduced pressure
dissolutionThe residue was dissolved in hexanes
washeluted with hexane

Sources & evidence

ORD record: ord-c49408fb85f948a8a4d5178edd03aafe
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07902203B2

Reaction notes

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