Water → 5-Bromo-4,6-dimethoxypyrimidine

HRID 271452Notes

Reaction equation

HRID 271452 reaction equation
[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]

Participants

6

Reactant 4

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

Product 1

HCID 5577185-Bromo-4,6-dimethoxypyrimidineYield 95.9%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-02df196805d546f59e0611ba62fe2b29
Source dataset
uspto-grants-2008_11
Patent number
US07452892B2

Reaction notes

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