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

HRID 601432노트

반응식

HRID 601432 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

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온도
90 °C

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-1e757ad5b018446ba53cd515c4fb6aa9
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07902203B2

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