Water → 1,3-dibenzyl-5-bromo-6-chloropyrimidine-2,4(1H,3H)-dione

HRID 271423노트

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HRID 271423 반응식
[Br:1][C:2]1[C:3](=[O:10])[NH:4][C:5](=O)[NH:6][C:7]=1[Cl:8].[C:11]([O-:14])([O-])=O.[K+].[K+].[CH2:17](Br)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.O>CN(C=O)C.CCOC(C)=O>[CH2:5]([N:6]1[C:7]([Cl:8])=[C:2]([Br:1])[C:3](=[O:10])[N:4]([CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:11]1=[O:14])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

참가 물질

7

반응물 4

HCID 962WaterHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 5898345-Bromo-6-chloropyrimidine-2,4-diol

생성물 1

HCID 598347971,3-dibenzyl-5-bromo-6-chloropyrimidine-2,4(1H,3H)-dione수율 97.5%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

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온도
75 °C

실험 절차

To a stirring solution of 5-bromo-6-chloropyrimidine-2,4(1H,3H)-dione (9.4 g, 41.7 mmol) in DMF (100 mL) at room temperature under argon was added K2CO3 (12.7 g, 91.8 mmol), followed by benzyl bromide (10.5 mL, 88.3 mmol). The reaction mixture was stirred at 75° C. for 1.5 h. After the reaction mixture was cooled to room temperature, water (100 mL) and EtOAc (150 mL) were added. The layers were separated. The organic layer was washed with water (50 mL×2), followed by saturated aqueous NaCl (50 mL), then dried (MgSO4) and concentrated at reduced pressure to obtain crude product. This crude product was passed through a bed of silica gel eluted with CH2Cl2 to obtain 16.5 g of the title compound as a white solid. HPLC/MS: retention time=3.818 min, [M+H]30 =405.

후처리

  1. temperatureAfter the reaction mixture was cooled to room temperature
  2. customThe layers were separated
  3. washThe organic layer was washed with water (50 mL×2)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated at reduced pressure
  6. customto obtain crude product
  7. washeluted with CH2Cl2

출처 및 근거

ORD 기록
ord-333c4ebb3d714d62b7e6062c48d45270
출처 데이터셋
uspto-grants-2008_11
특허 번호
US07452892B2

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