Sodium methanethiolate → 2-Chloro-4-(methylthio)pyrimidine

HRID 539900

Reaktionsgleichung

Reaktionsgleichung von HRID 539900
C([C:3]1[C:4](Cl)=[N:5][C:6]([Cl:9])=[N:7][CH:8]=1)C.[CH3:11][S-:12].[Na+]>O1CCCC1.C(OCC)(=O)C>[Cl:9][C:6]1[N:5]=[C:4]([S:12][CH3:11])[CH:3]=[CH:8][N:7]=1

Komponenten

5

Edukt 2

HCID 4378561Sodium methanethiolateHCID 100124582,4-Dichloro-5-ethylpyrimidine

Produkt 1

HCID 164271482-Chloro-4-(methylthio)pyrimidineAusbeute 53,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of ethyl 2,4-dichloropyrimidine (20.0 g, 0.13 mol) in 150 mL of anhydrous tetrahydrofurane was added sodium thiomethoxide (49.30 mL, 0.15 mol) at −10° C. The reaction mixture was allowed to warm up to room temperature and then stirred for 5 hours with monitoring a reaction with LC-MS or thin layer chromatography (TLC). The reaction mixture was diluted with ethyl acetate and washed with brine (×2). The collected organic layer was dried over anhydrous sodium sulfate and then concentrated in vacuo. The resulting solid was slurrified with diethyl ether and then collected by filtration to afford the desired intermediate 10 as a white solid (11.2 g, 52%)

Aufarbeitung

  1. customa reaction with LC-MS or thin layer chromatography (TLC)
  2. washwashed with brine (×2)
  3. dry with materialThe collected organic layer was dried over anhydrous sodium sulfate
  4. concentrationconcentrated in vacuo
  5. filtrationcollected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-4f1103dca1964454aec85ad23af160f0
Quelldatensatz
uspto-grants-2014_10
Patentnummer
US08871778B2

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