Water → 5-Bromo-4,6-dimethoxypyrimidine

HRID 271452Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 271452
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[N:6]=[CH:5][N:4]=1.CC(OC(C)=O)=O.C1C(=O)N([Br:25])C(=O)C1.O>CC(O)=O>[Br:25][C:8]1[C:3]([O:2][CH3:1])=[N:4][CH:5]=[N:6][C:7]=1[O:9][CH3:10]

Komponenten

6

Edukt 4

HCID 962WaterHCID 7918Acetic AnhydrideHCID 67184N-bromobutanimideHCID 2598214,6-Dimethoxypyrimidine

Produkt 1

HCID 5577185-Bromo-4,6-dimethoxypyrimidineAusbeute 95,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To the solution of 4,6-dimethoxypyrimidine (5 g, 35.7 mmol) in HOAc (20 mL) at room temperature under argon was added Ac2O (4.6 g, 44.6 mmol). The resulting solution was heated at 100° C. for 10 min and then NBS (7.9 g, 44.6 mmol) was added. Heating was continued at 100° C. for 5 h. Analysis by HPLC/MS indicated that the reaction was complete. After the reaction mixture was cooled to room temperature, water (50 mL) was added. The resulting precipitate was collected by filtration and further washed with water (15 mL×3), then dried under vacuum. The title compound (7.5 g) was obtained as a white solid. 1H NMR (CDCl3): δ 4.05 (s, 6H), 8.32 (s, 1H). 13C NMR (CDCl3): δ 55.2, 89.0, 154.9, 166.8.

Aufarbeitung

  1. temperatureHeating
  2. temperatureAfter the reaction mixture was cooled to room temperature
  3. filtrationThe resulting precipitate was collected by filtration
  4. washfurther washed with water (15 mL×3)
  5. customdried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-02df196805d546f59e0611ba62fe2b29
Quelldatensatz
uspto-grants-2008_11
Patentnummer
US07452892B2

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