Phosphorus oxychloride → 4-Chloro-6-methyl-2-(methylthio)pyrimidine

Reaktionsgleichung

O[C:2]1[CH:7]=[C:6]([CH3:8])[N:5]=[C:4]([S:9][CH3:10])[N:3]=1.P(Cl)(Cl)([Cl:13])=O>>[Cl:13][C:2]1[CH:7]=[C:6]([CH3:8])[N:5]=[C:4]([S:9][CH3:10])[N:3]=1

Komponenten

Edukt 2

HCID 24813Phosphorus oxychloride

HCID 178503447HCID 178503447, Verbindung

Produkt 1

HCID 2411634-Chloro-6-methyl-2-(methylthio)pyrimidineAusbeute 80 %

Versuchsvorschrift

4-Hydroxy-6-methyl-2-(methylthio)pyrimidine (9.20 g, 59 mmol) and phosphorous oxychloride (60 mL) were combined and refluxed for 3 hours. The reaction mixture was cooled to room temperature and poured onto crushed ice. The resultant aqueous mixture was extracted with ethyl acetate; and the organic layer washed with saturated aqueous sodium bicarbonate followed by a water wash, dried over magnesium sulfate, and dried in vacuo to give 4-chloro-6-methyl-2-(methylthio)pyrimidine (8.27 g, 80%), m.p. 37-38° C.

Aufarbeitung

temperaturerefluxed for 3 hours
additionpoured
customonto crushed ice
extractionThe resultant aqueous mixture was extracted with ethyl acetate
washand the organic layer washed with saturated aqueous sodium bicarbonate
washwash
dry with materialdried over magnesium sulfate
customdried in vacuo

Quellen und Nachweise

ORD-Eintrag: ord-cd5551f7f35444d0abf193a41b49fc09
Quelldatensatz: uspto-grants-1999_09
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US05952331

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