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

HRID 709972

反応式

HRID 709972 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>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

5

反応物 3

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

生成物 1

HCID 1387273-Methyl-2-(methylthio)-4(3H)-pyrimidinone収率 62.2%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

A 0° C. suspension of 2-(methylthio)pyrimidin-4(3H)-one (2.0 g, 14.1 mmol) in DMF (40 mL) was treated with solid LiHMDS (3.06 g, 18.3 mmol), followed by methyl iodide (1.14 mL, 18.3 mmol), warmed to RT and stirred overnight. The mixture was quenched with water, extracted with EtOAc (3×) and the combined organics were dried over Na2SO4, concentrated to dryness and purified via silica gel chromatography (EtOAc/Hex) to afford 3-methyl-2-(methylthio)pyrimidin-4(3H)-one (1.37 g, 62%). 1H NMR (400 MHz, DMSO-d6): δ 7.83 (d, J=6.5 Hz, 1H), 6.17 (d, J=6.5 Hz, 1H), 3.39 (s, 3H), 2.54 (s, 3H); MS (ESI) m/z: 157.1 (M+H+).

後処理

  1. customThe mixture was quenched with water
  2. extractionextracted with EtOAc (3×)
  3. dry with materialthe combined organics were dried over Na2SO4
  4. concentrationconcentrated to dryness
  5. custompurified via silica gel chromatography (EtOAc/Hex)

出典と根拠

ORDレコード
ord-ba872198cc934377b4d46c19bd45c718
出典データセット
uspto-grants-2015_11
特許番号
US09181223B2

関連ノート

読み込み中…