Pyridine → n-(6-chloro-2-methylpyrimidin-4-yl)acetamide

HRID 1811899Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1811899
[Cl:1][C:2]1[N:7]=[C:6]([CH3:8])[N:5]=[C:4]([NH2:9])[CH:3]=1.N1C=CC=CC=1.[C:16](OC(=O)C)(=[O:18])[CH3:17]>C([O-])(O)=O.[Na+]>[Cl:1][C:2]1[N:7]=[C:6]([CH3:8])[N:5]=[C:4]([NH:9][C:16](=[O:18])[CH3:17])[CH:3]=1

Komponenten

5

Edukt 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 2867546-Chloro-2-methylpyrimidin-4-amine

Produkt 1

HCID 243561n-(6-chloro-2-methylpyrimidin-4-yl)acetamideAusbeute 71 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 516892Sodium BicarbonateLösungsmittel

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

A mixture of 6-chloro-2-methylpyrimidin-4-amine (500 mg, 3483 μmol), pyridine (568 μl, 6965 μmol), and acetic anhydride (493 μl, 5224 μmol) was stirred at 40° C. for 24 h. The mixture was cooled down to rt. The reaction mixture was diluted with saturated NaHCO3 (30 mL) and extracted with EtOAc (2×40 mL). The organic extract was washed with saturated NaCl (about2 mL), dried over Na2SO4, filtered, concentrated in vacuo and the residue was purified by silica gel chromatography eluting with 40% EtOAc/hexanes to give N-(6-chloro-2-methylpyrimidin-4-yl)acetamide (458 mg, 71% yield). 1H NMR (300 MHz, CDCl3) δ 8.03 (s, 1H); 7.90 (s, 1H); 2.58 (s, 3H); 2.23 (s, 3H). m/z (ESI, +ve ion) 186 (M+H)+.

Aufarbeitung

  1. temperatureThe mixture was cooled down to rt
  2. extractionextracted with EtOAc (2×40 mL)
  3. extractionThe organic extract
  4. washwas washed with saturated NaCl (about2 mL)
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customthe residue was purified by silica gel chromatography
  9. washeluting with 40% EtOAc/hexanes

Quellen und Nachweise

ORD-Eintrag
ord-94ea20e2e55d410b9eb69dc122b55254
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08362241B2

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