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

HRID 601432ノート

反応式

HRID 601432 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

反応条件

温度
90 °C

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-1e757ad5b018446ba53cd515c4fb6aa9
出典データセット
uspto-grants-2011_03
特許番号
US07902203B2

反応ノート

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