2,4-Dichloro-6-methyl-5-nitropyrimidine → 2-Chloro-4-methoxy-6-methyl-5-nitropyrimidine

HRID 598058Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 598058
[Cl:1][C:2]1[N:7]=[C:6](Cl)[C:5]([N+:9]([O-:11])=[O:10])=[C:4]([CH3:12])[N:3]=1.[CH3:13][O-:14].[Na+]>CO>[Cl:1][C:2]1[N:7]=[C:6]([O:14][CH3:13])[C:5]([N+:9]([O-:11])=[O:10])=[C:4]([CH3:12])[N:3]=1

Komponenten

4

Edukt 2

HCID 2752942,4-Dichloro-6-methyl-5-nitropyrimidineHCID 10942334Sodium Methoxide

Produkt 1

HCID 130809792-Chloro-4-methoxy-6-methyl-5-nitropyrimidineAusbeute 65,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
-10 °C

Versuchsvorschrift

2,4-Dichloro-6-methyl-5-nitropyrimidine (3.0 g, 14.4 mmol) was dissolved in methanol (30 mL). The solution was cooled to −10° C. and sodium methoxide (25% in methanol, 3.3 mL, 14.4 mmol) was added drop wise. After 10 minutes, the solution was quenched with acetic acid (5 mL) and concentrated. The residue was suspended in saturated sodium bicarbonate and extracted twice with ethyl acetate. The organic layer was dried over sodium sulfate, filtered and concentrated. Flash chromatography (5% ethyl acetate/hexanes) gave 1.91 g (65% yield) of the title compound as a white solid.

Aufarbeitung

  1. customthe solution was quenched with acetic acid (5 mL)
  2. concentrationconcentrated
  3. extractionextracted twice with ethyl acetate
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-29520bfb21f447d98738019874294ace
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07897607B2

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