N-Methyl-m-anisidine → 4-(N-Methyl-3-methoxyanilino)-2-(2-pyridinyl)-6-trifluoromethyl-pyrimidine

HRID 1765256Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1765256
Cl[C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[N:5]=[C:4]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=2)[N:3]=1.[CH3:18][NH:19][C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([O:26][CH3:27])[CH:21]=1>>[CH3:18][N:19]([C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[N:5]=[C:4]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=2)[N:3]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([O:26][CH3:27])[CH:21]=1

Komponenten

3

Edukt 2

HCID 84349N-Methyl-m-anisidineHCID 113115004-Chloro-2-(2-pyridinyl)-6-(trifluoromethyl)pyrimidine

Produkt 1

HCID 227323924-(N-Methyl-3-methoxyanilino)-2-(2-pyridinyl)-6-trifluoromethyl-pyrimidineAusbeute 100 %

Versuchsvorschrift

A mixture of 4-chloro-2-(2-pyridinyl)-6-trifluoromethyl-pyrimidine (180 mg, 0.693 mmol) and N-methyl-3-methoxyaniline (112 mg, 0.816 mmol) in 3 mL of solvent (ethanol:water=2:1) was refluxed for 20 h. The solvent was removed under reduced pressure and the residue was dissolved in 25 mL of ethyl acetate. The ethyl acetate solution was washed with 25 mL of 1M NaOH, and the aqueous layer was reextracted with ethyl acetate (25 mL). The combined organic extracts were washed with saturated NaCl and dried over Na2SO4, filtered and concentrated. The crude product was purified by flash column chromatography (40–45% ethyl acetate/hexanes) to give the title compound as an oil (250 mg, 0.693 mmol, 100%). 1H NMR (CDCl3): 8.86 (dd, J=0.6, 4.5 Hz, 1H), 8.50 (d, J=7.5 Hz, 1H), 7.85 (dt, J=1.8, 7.8 Hz, 1H), 7.42 (m, 2H), 6.95 (dd, J=1.8, 8.4 Hz, 1H), 6.86 (m, 1H), 6.82 (m. 1H), 3.85 (s, 3H), 3.68 (s, 3H).

Aufarbeitung

  1. temperaturewas refluxed for 20 h
  2. customThe solvent was removed under reduced pressure
  3. dissolutionthe residue was dissolved in 25 mL of ethyl acetate
  4. washThe ethyl acetate solution was washed with 25 mL of 1M NaOH
  5. washThe combined organic extracts were washed with saturated NaCl
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe crude product was purified by flash column chromatography (40–45% ethyl acetate/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-9a3905b8e2634fc295b8f3dab493c29b
Quelldatensatz
uspto-grants-2007_06
Patentnummer
US07226927B2

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