Water → 5-Bromo-4,6-dimethoxypyrimidine

HRID 271452노트

반응식

HRID 271452 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 176Acetic Acid용매

반응 조건

온도
100 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-02df196805d546f59e0611ba62fe2b29
출처 데이터셋
uspto-grants-2008_11
특허 번호
US07452892B2

반응 노트

불러오는 중…