Dimethylformamide → HCID 67329637, Verbindung

HRID 1846193Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1846193
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH3:9])[N:6]=C(N)[N:4]=1.CI.[H-].[Na+].[CH3:15][N:16]([CH:18]=O)[CH3:17]>>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH3:9])[N:6]=[C:18]([N:16]([CH3:15])[CH3:17])[N:4]=1

Komponenten

5

Edukt 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 5872364-Methoxy-6-methylpyrimidin-2-amine

Produkt 1

HCID 67329637HCID 67329637, Verbindung

Reaktionsbedingungen

Temperatur
23 °C

Versuchsvorschrift

To a stirred solution containing 1.0 g (7.19 mmol) of 4-methoxy-6-methylpyrimidin-2-amine in 10 mL of anf DMF were added 1.35 mL (21.6 mmol) of methyl iodide followed by 853 mg (21.6 mmol) of 60% suspension of sodium hydride in mineral oil. The reaction mixture was stirred at 23° C. for 20 min. The reaction mixture was quenched with water and concentrated under diminished pressure in order to remove as much DMF as possible. The residue was dissolved in 70 mL of ethyl acetate and washed with 50-mL portions of water and brine respectively. The organic solution was dried (MgSO4) and concentrated under diminished pressure. The residue was purified by chromatography on a silica gel column (15×5 cm). Elution with 4:1 hexanes-ethyl acetate afforded the expected product as colorless oil: yield 755 mg (63%); silica gel TLC Rf 0.25 (4:1 hexanes-ethyl acetate); 1H NMR (CDCl3) δ 2.22 (s, 3H), 3.12 (s, 6H), 3.83 (s, 3H) and 5.76 (s, 1H); 13C-NMR (CDCl3) δ 24.07, 36.76, 36.76, 52.68, 93.74, 162.24, 167.70 and 170.24; mass spectrum (APCI+), m/z 168.1135 (M+H) (C8H14N3O requires 168.1137).

Aufarbeitung

  1. customThe reaction mixture was quenched with water
  2. concentrationconcentrated under diminished pressure in order
  3. customto remove as much DMF as possible
  4. dissolutionThe residue was dissolved in 70 mL of ethyl acetate
  5. washwashed with 50-mL portions of water and brine respectively
  6. dry with materialThe organic solution was dried (MgSO4)
  7. concentrationconcentrated under diminished pressure
  8. customThe residue was purified by chromatography on a silica gel column (15×5 cm)
  9. washElution with 4:1 hexanes-ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-4f5f8ab2dd5944cebdadf0ff5de59298
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08952025B2

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