Dimethylformamide → 1-{[5-(Chloromethyl)pyrazin-2-yl]methyl}-3-bromo-4-[(2,4-difluorobenzyl)oxy]-6-methylpyridin-2(1H)-one

HRID 1832004Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1832004
N1C(Cl)=NC(Cl)=NC=1[Cl:3].CN(C=O)C.[Br:15][C:16]1[C:17](=[O:42])[N:18]([CH2:33][C:34]2[CH:39]=[N:38][C:37]([CH2:40]O)=[CH:36][N:35]=2)[C:19]([CH3:32])=[CH:20][C:21]=1[O:22][CH2:23][C:24]1[CH:29]=[CH:28][C:27]([F:30])=[CH:26][C:25]=1[F:31]>ClCCl>[Br:15][C:16]1[C:17](=[O:42])[N:18]([CH2:33][C:34]2[CH:39]=[N:38][C:37]([CH2:40][Cl:3])=[CH:36][N:35]=2)[C:19]([CH3:32])=[CH:20][C:21]=1[O:22][CH2:23][C:24]1[CH:29]=[CH:28][C:27]([F:30])=[CH:26][C:25]=1[F:31]

Komponenten

5

Edukt 3

HCID 6228Dimethylformamide2×HCID 7954Cyanuric chlorideHCID 220506073-Bromo-4-[(2,4-difluorobenzyl)oxy]-1-{[5-(hydroxymethyl)pyrazin-2-yl]methyl}-6-methylpyridin-2(1H)-one

Produkt 1

HCID 220511691-{[5-(Chloromethyl)pyrazin-2-yl]methyl}-3-bromo-4-[(2,4-difluorobenzyl)oxy]-6-methylpyridin-2(1H)-oneAusbeute 77 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

Cyanurylchloride (0.42 g, .0023 mol) was added to DMF (0.52 mL) and stirred at room temperature for 15 min. Then added dichloromethane (15 mL) followed by the addition of 3-Bromo-4-[(2,4-difluorobenzyl)oxy]-1-{[5-(hydroxymethyl)pyrazin-2-yl]methyl}-6-methylpyridin-2(1H)-one 1.0 g, 0.0022 mol) and reaction mixture was stirred at room temperature under argon atmosphere. After 1 h, an additional 1.0 mL of DMF was added and the reaction was allowed to proceed for another hour, when a clear solution was obtained. The solution was diluted with dichloromethane (20 mL) and washed with water, dried (Na2SO4), and concentrated to dryness under reduced pressure. The residue was triturated with EtOAc, filtered, washed with EtOAc and dried to afford 0.79 g (77%) of the title compound as a pale yellow powder: 1H NMR (CD3OD/400 MHz) δ 8.66 (s, 2H), 7.73 (m, 1H), 7.05 (m, 2H), 6.56 (s, 1H), 5.52 (s, 2H), 5.33 (s, 2H), 4.74 (s, 2H), and 2.57 (s, 3H); ES-HRMS m/z 470.0051 (M+H C19H16N3O2BrClF2 requires 470.0077).

Aufarbeitung

  1. customreaction mixture
  2. stirringwas stirred at room temperature under argon atmosphere
  3. waitAfter 1 h
  4. waitto proceed for another hour
  5. customwhen a clear solution was obtained
  6. washwashed with water
  7. dry with materialdried (Na2SO4)
  8. concentrationconcentrated to dryness under reduced pressure
  9. customThe residue was triturated with EtOAc
  10. filtrationfiltered
  11. washwashed with EtOAc
  12. customdried

Quellen und Nachweise

ORD-Eintrag
ord-04370ab382ad46b6b944af5251cf3507
Quelldatensatz
uspto-grants-2006_06
Patentnummer
US07067540B2

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