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

HRID 1398867Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1398867
[CH3:1][O-:2].[Na+].Cl[C:5]1[N:10]=[C:9]([Cl:11])[C:8]([N+:12]([O-:14])=[O:13])=[C:7]([CH3:15])[N:6]=1>CO.O>[Cl:11][C:9]1[C:8]([N+:12]([O-:14])=[O:13])=[C:7]([CH3:15])[N:6]=[C:5]([O:2][CH3:1])[N:10]=1

Komponenten

5

Edukt 2

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

Produkt 1

HCID 130809804-Chloro-2-methoxy-6-methyl-5-nitropyrimidineAusbeute 25,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Sodium methoxide (28% solution in methanol, 47.0 g, 244 mmol) was added dropwise to a stirred solution of 2,4-dichloro-6-methyl-5-nitropyrimidine (48.3 g, 232 mmol) in methanol (600 mL) at 0° C., and the mixture was stirred at 0° C. for 30 min. The mixture was diluted with water, concentrated, and extracted with ethyl acetate. The combined organic layer was washed with brine, dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel eluting with a 0-15% ethyl acetate/n-hexane gradient mixture. The filtrate was concentrated in vacuo to give the title compound as a yellow solid (11.9 g, 58.5 mmol, 25%).

Aufarbeitung

  1. concentrationconcentrated
  2. extractionextracted with ethyl acetate
  3. washThe combined organic layer was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by flash column chromatography on silica gel eluting with a 0-15% ethyl acetate/n-hexane gradient mixture
  8. concentrationThe filtrate was concentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-b2e50060e1244ab59c44ff4aec67228a
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08901141B2

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