Dimethyl Carbonate → 6-bromo-1H,2H,4H-pyrido(2,3-d)(1,3)oxazin-2-one

HRID 1710537Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1710537
[NH2:1][C:2]1[C:7]([CH2:8][OH:9])=[CH:6][C:5]([Br:10])=[CH:4][N:3]=1.[C:11](=O)(OC)[O:12]C.C[O-].[Na+]>CO>[Br:10][C:5]1[CH:4]=[N:3][C:2]2[NH:1][C:11](=[O:12])[O:9][CH2:8][C:7]=2[CH:6]=1

Komponenten

5

Edukt 3

HCID 12021Dimethyl CarbonateHCID 108913662-Amino-5-bromo-3-(hydroxymethyl)pyridineHCID 10942334Sodium Methoxide

Produkt 1

HCID 159259906-bromo-1H,2H,4H-pyrido(2,3-d)(1,3)oxazin-2-oneAusbeute 51 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To a stirred solution of 2-amino-5-bromo-3-(hydroxymethyl)pyridine (3.0 g, 15 mmole) in methanol (30 mL) was added dimethyl carbonate (5 mL, 60 mmole) and sodium methoxide (25 wt % solution in methanol, 4 mL, 17.4 mmole). The reaction was heated at reflux for 18 hr, cooled to RT, and concentrated to dryness. The remaining residue was triturated with saturated aqueous NH4Cl (50 mL), filtered, washed with cold H2O (50 mL), and dried under vacuum to give the title compound (1.75 g, 51%) as a beige solid: LCMS (ES) m/e 229.0 (M+H)+; 1H NMR (400 MHz, DMSO-d6) δ 10.90 (s, 1H), 8.31 (s, 1H), 7.90 (s, 1H), 5.31 (s, 2H).

Aufarbeitung

  1. temperatureThe reaction was heated
  2. temperatureat reflux for 18 hr
  3. concentrationconcentrated to dryness
  4. customThe remaining residue was triturated with saturated aqueous NH4Cl (50 mL)
  5. filtrationfiltered
  6. washwashed with cold H2O (50 mL)
  7. customdried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-b7fbfb6af76543fe8b8008dbc360b648
Quelldatensatz
uspto-grants-2010_09
Patentnummer
US07790716B2

Notizen zur Reaktion

Wird geladen…