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Methyl iodide → 2-methylthio-5-(2-hydroxyethyl)-3,6-dimethyl-3H-pyrimidin-4-one

HRID 2222279
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2222279
[CH3:1][S:2][C:3]1[NH:8][C:7](=[O:9])[C:6]([CH2:10][CH2:11][OH:12])=[C:5]([CH3:13])[N:4]=1.[H-].[Na+].[CH3:16]I>CN(C=O)C>[CH3:1][S:2][C:3]1[N:8]([CH3:16])[C:7](=[O:9])[C:6]([CH2:10][CH2:11][OH:12])=[C:5]([CH3:13])[N:4]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 1354111545-(2-hydroxyethyl)-6-methyl-2-(methylsulfanyl)-4(3H)-pyrimidinone

Produkt 1

HCID 693142522-methylthio-5-(2-hydroxyethyl)-3,6-dimethyl-3H-pyrimidin-4-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

To a suspension of 2-methylthio-5-(2-hydroxyethyl)-6-methyl-3H-pyrimidin-4-one (34 g, 0.17 mol) in DMF (300 ml) was added slowly one equivalent of sodium hydride (55%, 7.4 g). Next was added slowly one equivalent of methyl iodide (10.5 ml). The mixture was stirred for two hours at 50° C., after which most of the DMF was removed in vaccuum. Water was added and the mixture was extracted with ethyl acetate. The combined organic layer was dried over sodium sulfate and then concentrated and purified by flash chromatografy (eluens: ether followed by ether/methanol=9/1). Yield 20.3 g (56%), mp. 117-118° C.

Aufarbeitung

  1. customafter which most of the DMF was removed in vaccuum
  2. additionWater was added
  3. extractionthe mixture was extracted with ethyl acetate
  4. dry with materialThe combined organic layer was dried over sodium sulfate
  5. concentrationconcentrated
  6. custompurified by flash chromatografy (eluens: ether followed by ether/methanol=9/1)

Quellen und Nachweise

ORD-Eintrag
ord-d35b47aa00154a578d283e4c3cb4713a
Quelldatensatz
uspto-grants-2008_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07371769B2

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