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

HRID 271423

反応式

HRID 271423 の反応式
[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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
75 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-333c4ebb3d714d62b7e6062c48d45270
出典データセット
uspto-grants-2008_11
特許番号
US07452892B2

関連ノート

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