Iodoethane → N-(4-iodophenyl)-N-ethylpyrimidin-2-amine

HRID 1360043Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1360043
[I:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[N:14]=[CH:13][CH:12]=[CH:11][N:10]=2)=[CH:4][CH:3]=1.[H-].[Na+].[CH2:17](I)[CH3:18]>CN(C=O)C.[Cl-].[Na+].O>[I:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]([CH2:17][CH3:18])[C:9]2[N:10]=[CH:11][CH:12]=[CH:13][N:14]=2)=[CH:6][CH:7]=1

Komponenten

6

Edukt 3

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 57762548N-(4-iodophenyl)pyrimidin-2-amine

Produkt 1

HCID 57762566N-(4-iodophenyl)-N-ethylpyrimidin-2-amine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittel2×HCID 57417360Sodium chloride; waterLösungsmittel

Versuchsvorschrift

Under an argon atmosphere, a solution of N-(4-iodophenyl)pyrimidin-2-amine (255 mg) in anhydrous DMF (1 ml) was added dropwise to a suspension of sodium hydride (40 mg) in anhydrous DMF (1 ml), and the resulting mixture was stirred at room temperature for 75 minutes. Ethyl iodide (0.10 ml) was added dropwise to the reaction solution and the resulting mixture was stirred at room temperature overnight. Saturated brine was added thereto and the resulting mixture was extracted with chloroform. Organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. After removing anhydrous sodium sulfate by filtration, the filtrate was concentrated. The residue was purified by column chromatography (silica gel, eluent:cyclohexane/chloroform=1/10) to obtain N-(4-iodophenyl)-N-ethylpyrimidin-2-amine (264 mg). NMR (H1, CDCl3): δ 1.23 (3H, t, J=6.8 Hz), 4.01 (2H, q, J=6.8 Hz), 6.57 (1H, t, J=4.9 Hz), 7.03-7.06 (2H, m), 7.70-7.74 (2H, m), 8.32 (2H, d, J=4.9 Hz)

Aufarbeitung

  1. stirringthe resulting mixture was stirred at room temperature overnight
  2. extractionthe resulting mixture was extracted with chloroform
  3. washOrganic layer was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customAfter removing anhydrous sodium sulfate
  6. filtrationby filtration
  7. concentrationthe filtrate was concentrated
  8. customThe residue was purified by column chromatography (silica gel, eluent:cyclohexane/chloroform=1/10)

Quellen und Nachweise

ORD-Eintrag
ord-ce3d89afbd2e461aa71a726a7d29d0a3
Quelldatensatz
uspto-grants-2011_02
Patentnummer
US07879837B2

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