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

HRID 225890Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 225890
[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 tide 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, 1 H), 8.31 (s, 1 H), 7.90 (s, 1 H), 5.31 (s, 2 H).

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-fc6d7749128a45e783989defb5223586
Quelldatensatz
uspto-grants-2009_07
Patentnummer
US07557125B2

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