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

HRID 709972

반응식

HRID 709972 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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+).

후처리

  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)

출처 및 근거

ORD 기록
ord-ba872198cc934377b4d46c19bd45c718
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09181223B2

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