Water → 5-bromo-3-(4-methoxybenzyl)pyrimidin-4(3H)-one

HRID 910610ノート

反応式

HRID 910610 の反応式
[Br:1][C:2]1[C:3](=[O:8])[NH:4][CH:5]=[N:6][CH:7]=1.[H-].[Na+].Cl[CH2:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=1.O>CN(C)C=O>[Br:1][C:2]1[C:3](=[O:8])[N:4]([CH2:12][C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=2)[CH:5]=[N:6][CH:7]=1

参加物

6

反応物 4

HCID 962WaterHCID 24758Sodium hydrideHCID 699934-Methyloxybenzyl chlorideHCID 882564(3H)-Pyrimidinone, 5-bromo-

生成物 1

HCID 575841305-bromo-3-(4-methoxybenzyl)pyrimidin-4(3H)-one

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

5-Bromopyrimidin-4(3H)-one (459 mg) was dissolved in N,N-dimethylformamide (13 mL), then with cooling with ice, sodium hydride (55%, 137 mg) was added, followed by stirring at the same temperature for 30 minutes. Then, 1-(chloromethyl)-4-methoxybenzene (392 μL) was added, followed by stirring at room temperature for 15 hours. Water was added to the reaction mixture, followed by extraction with chloroform. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1 to 2:1) to obtain 5-bromo-3-(4-methoxybenzyl)pyrimidin-4(3H)-one (382 mg) as a white solid.

後処理

  1. additionwas added
  2. stirringby stirring at room temperature for 15 hours
  3. extractionfollowed by extraction with chloroform
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. customthe resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1 to 2:1)

出典と根拠

ORDレコード
ord-8e4892decde845ecb2eceb4192b6efe4
出典データセット
uspto-grants-2011_09
特許番号
US08022208B2

反応ノート

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