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

HRID 601432Notes

Reaction equation

HRID 601432 reaction equation
[CH:1]1([CH2:5][N:6]2[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][C:7]2=[O:13])[CH2:4][CH2:3][CH2:2]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:8]1[C:9](=[O:12])[CH:10]=[CH:11][N:6]([CH2:5][CH:1]2[CH2:2][CH2:3][CH2:4]2)[C:7]1=[O:13]

Participants

5

Reactant 3

HCID 1049PyridineHCID 24976308Tris(methylthio)methyl methyl sulfateHCID 670645871-(cyclobutylmethyl)-4-hydroxy-2(1H)-pyridinone

Product 1

HCID 104690703-[bis(methylsulfanyl)methylene]-1-(cyclobutylmethyl)-2,4(1H,3H)-pyridinedioneYield 50%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

A solution of the product of Example 468B (0.244 g, 1.36 mmol) and pyridine (0.88 mL, 10.89 mmol) in dioxane (6 mL) 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 a stream of warm nitrogen. The residue was dissolved in hexanes and loaded onto a 2 g Alltech Seppack and eluted with hexanes followed by dichloromethane followed by 25% ethyl acetate in dichloromethane to provide the title compound (0.192 g, 50%).

Workup

  1. customprepared
  2. customin Synthesis, 22-25, 1988
  3. temperaturecooled to about 25° C
  4. customThe reaction solution was decanted from the resulting solids
  5. customthe solvent was removed under a stream of warm nitrogen
  6. dissolutionThe residue was dissolved in hexanes
  7. washeluted with hexanes

Sources & evidence

ORD record
ord-1e757ad5b018446ba53cd515c4fb6aa9
Source dataset
uspto-grants-2011_03
Patent number
US07902203B2

Reaction notes

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