Sodium hydride → 1-(Pyrimidin-2-yl)-1H-imidazole-4-carbaldehyde

HRID 50557

Reaktionsgleichung

Reaktionsgleichung von HRID 50557
[H-].[Na+].[NH:3]1[CH:7]=[C:6]([CH:8]=[O:9])[N:5]=[CH:4]1.Cl[C:11]1[N:16]=[CH:15][CH:14]=[CH:13][N:12]=1>CN(C=O)C>[N:12]1[CH:13]=[CH:14][CH:15]=[N:16][C:11]=1[N:3]1[CH:7]=[C:6]([CH:8]=[O:9])[N:5]=[CH:4]1

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 744042-ChloropyrimidineHCID 764281H-Imidazole-4-carbaldehyde

Produkt 1

HCID 226308841-(Pyrimidin-2-yl)-1H-imidazole-4-carbaldehydeAusbeute 99 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Sodium hydride (60% in oil, 1.44 g, 36.00 mmol) was added to a 0° C. solution of 1H-imidazole-4-carboxaldehyde (4.40 g, 36.03 mmol) in DMF (16 mL). After stirring for 20 min at 0° C., the mixture was allowed to warm to RT and a solution of 2-chloropyrimidine (4.12 g, 35.97 mmol) in DMF (8 mL) was added. The resulting mixture was heated to 100° C. for 18 h. The solvent was evaporated, the residue was dissolved in ethyl acetate, washed with water and brine, dried (MgSO4), and concentrated to provide 6.20 g (86%) of the title compound. MS 175 (M+H)+.

Aufarbeitung

  1. temperatureto warm to RT
  2. temperatureThe resulting mixture was heated to 100° C. for 18 h
  3. customThe solvent was evaporated
  4. dissolutionthe residue was dissolved in ethyl acetate
  5. washwashed with water and brine
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-eab46b298713425b9b721e11ac398b2c
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06713455B2

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