Water → 3-Methyl-2-(methylthio)-4(3H)-pyrimidinone

HRID 1993344

反応式

HRID 1993344 の反応式
[CH3:1][S:2][C:3]1[NH:8][C:7](=[O:9])[CH:6]=[CH:5][N:4]=1.[Li+].[CH3:11][Si]([N-][Si](C)(C)C)(C)C.CI.O>CN(C=O)C>[CH3:11][N:8]1[C:7](=[O:9])[CH:6]=[CH:5][N:4]=[C:3]1[S:2][CH3:1]

参加物

6

反応物 4

HCID 962WaterHCID 6328Methyl iodideHCID 798232-(Methylthio)-1H-pyrimidin-4-oneHCID 2733832Lithium Hexamethyldisilazide

生成物 1

HCID 1387273-Methyl-2-(methylthio)-4(3H)-pyrimidinone

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

反応条件

温度
0 °C

実験手順

2-Methylthio-3H-pyrimidin-4-one (Step 1, 6.29 g, 44.2 mmol) was suspended in DMF (100 mL), cooled to 0° C., and additional DMF (50 mL) was added. Solid LiHMDS (9.58 g, 57.3 mmol) was added in one portion, and the reaction was stirred at 0° C. MeI (3.6 mL, 57.8 mmol) was added via syringe, and the reaction was warmed to RT and stirred for 20.75 h. At this time, the mixture was poured into 300 mL H2O and extracted exhaustively with EtOAc. The organic extracts were combined, dried over Na2SO4, filtered, concentrated, and purified on silica gel (3:1→3:2→1:1 hexanes/EtOAc) to give the title compound. MS (ESI pos. ion) m/z: 157. Calc'd for C6H8N2OS: 156.04.

後処理

  1. temperaturethe reaction was warmed to RT
  2. stirringstirred for 20.75 h
  3. extractionextracted exhaustively with EtOAc
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. custompurified on silica gel (3:1→3:2→1:1 hexanes/EtOAc)

出典と根拠

ORDレコード
ord-659dea8943cd4f6a92aba0c5d25cfd6a
出典データセット
uspto-grants-2010_01
特許番号
US07652009B2

関連ノート

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