Dimethylformamide → 4,6-Dichloro-2-(methylsulfanyl)pyrimidine-5-carbaldehyde

HRID 2243640

Reaktionsgleichung

Reaktionsgleichung von HRID 2243640
P(Cl)(Cl)([Cl:3])=O.CN([CH:9]=[O:10])C.O[C:12]1[NH:17][C:16]([S:18][CH3:19])=[N:15]C(=O)C=1.Cl[CH:22]=[C:23]([Cl:25])Cl>>[Cl:25][C:23]1[C:22]([CH:9]=[O:10])=[C:12]([Cl:3])[N:17]=[C:16]([S:18][CH3:19])[N:15]=1

Komponenten

5

Edukt 4

HCID 6228DimethylformamideHCID 6575TrichloroethyleneHCID 24813Phosphorus oxychlorideHCID 178503560HCID 178503560, Verbindung

Produkt 1

HCID 46140044,6-Dichloro-2-(methylsulfanyl)pyrimidine-5-carbaldehydeAusbeute 61 %

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To the solution of phosphorus oxychloride (65 mL, 0.70 mol) in trichloroethylene (46.5 mL) was added DMF (25 mL, 0.32 mol) slowly to keep the temperature between 5° C. to 10° C. The solution was then warmed up to room temperature before 6-hydroxy-2-(methylthio)-4(1H)-pyrimidinone (25 g, 0.16 mol) was added in portions. The resultant reaction mixture was heated at 80° C. overnight followed by concentration under vacuum. The resulting slurry like residue was poured into ice, stirred for about 2 hours then filtered to afford the crude product. The crude product was further purified by recrystalization with hexane to afford 4,6-dichloro-2-(methylthio)-5-pyrimidinecarbaldehyde (21.3 g, 61%). 1H-NMR (CDCl3) δ 2.66 (s, 3H), 10.4 (s, 1H).

Aufarbeitung

  1. custombetween 5° C. to 10° C
  2. additionwas added in portions
  3. customThe resultant reaction mixture
  4. concentrationfollowed by concentration under vacuum
  5. additionThe resulting slurry like residue was poured into ice
  6. filtrationthen filtered
  7. customto afford the crude product
  8. customThe crude product was further purified by recrystalization with hexane

Quellen und Nachweise

ORD-Eintrag
ord-88fd5dd53fdd411eb56c49f02b0acb0a
Quelldatensatz
uspto-grants-2010_03
Patentnummer
US07674789B2

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