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

HRID 1993344

Reaktionsgleichung

Reaktionsgleichung von HRID 1993344
[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]

Komponenten

6

Edukt 4

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

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.

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-659dea8943cd4f6a92aba0c5d25cfd6a
Quelldatensatz
uspto-grants-2010_01
Patentnummer
US07652009B2

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