2-Chloro-5-nitropyrimidine → 2-Methoxy-5-nitropyrimidine

HRID 450179

Reaktionsgleichung

Reaktionsgleichung von HRID 450179
[CH3:1][O-:2].[Na+].Cl[C:5]1[N:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][N:6]=1>CO>[CH3:1][O:2][C:5]1[N:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][N:6]=1

Komponenten

4

Edukt 2

HCID 825442-Chloro-5-nitropyrimidineHCID 10942334Sodium Methoxide

Produkt 1

HCID 3529002-Methoxy-5-nitropyrimidineAusbeute 134,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To a solution of sodium methoxide (0.090 g of sodium) in MeOH (12 mL) was added 0.486 g (3.03 mmol) of 2-chloro-5-nitropyrimidine, and the mixture was heated under reflux for 1 hr. After cooling, the mixture was concentrated in vacuo, extracted with EtOAc, and washed with water. The aqueous layer was extracted with CHCl3 and the combined organic layers were dried (Na2SO4), and concentrated, to give 0.347 g (75% yield) of 2-methoxy-5-nitropyrimidine as a yellow powder: 1H NMR (CDCl3) δ9.31 (s, 2H), 4.17 (s, 3H); LCMS (APCI+) m/z: 156 (MH+, 100%).

Aufarbeitung

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 1 hr
  3. temperatureAfter cooling
  4. concentrationthe mixture was concentrated in vacuo
  5. extractionextracted with EtOAc
  6. washwashed with water
  7. extractionThe aqueous layer was extracted with CHCl3
  8. dry with materialthe combined organic layers were dried (Na2SO4)
  9. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-160f4f9dca0f416a938b965dced57a0a
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08486939B2

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