氢化钠 → (+)-2-{4-(1-Hexyloxyethyl)phenyl}-5-decyloxypyrimidine

HRID 274177

反应方程式

HRID 274177 反应方程式
[OH:1][CH:2]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[N:15]=[CH:14][C:13]([O:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])=[CH:12][N:11]=2)=[CH:6][CH:5]=1)[CH3:3].[H-].[Na+].[C:29]1(C)[CH:34]=[CH:33][C:32](S(OCCCCCC)(=O)=O)=[CH:31][CH:30]=1>O>[CH2:33]([O:1][CH:2]([C:4]1[CH:5]=[CH:6][C:7]([C:10]2[N:15]=[CH:14][C:13]([O:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])=[CH:12][N:11]=2)=[CH:8][CH:9]=1)[CH3:3])[CH2:34][CH2:29][CH2:30][CH2:31][CH3:32]

参与物

5

反应物 3

HCID 24758氢化钠HCID 2204482-氰基苯甲酸HCID 214682802-(4-(1-Hydroxyethyl)phenyl)-5-decyloxypyrimidine

产物 1

HCID 54404658(+)-2-{4-(1-Hexyloxyethyl)phenyl}-5-decyloxypyrimidine收率 82.1%

试剂、催化剂与溶剂 1

HCID 962聚[6-[4-(4-氰基苯基)苯氧基]己基甲基丙烯酸酯]溶剂

反应条件

温度
40 °C

实验过程

Into 20 ml of anhydrous dlmethylformamide were dissolved 1.78 g (5 millimole) of the (+)-2-{4-(1-hydroxyethyl)phenyl}-5-decyloxypyrimidine obtained in Preparation Example [starting material compound (VI)] 70, and then 0.24 g (6 millimole) of 60% sodium hydride was added thereto, followed by stirring at 40° C. for 1 hour. Subsequently, 1.79 g (7 millimole) of hexyl p-toluenesulfonate were added thereto, to subject to reaction at the same temperature for 2 hours. After completion of the reaction, the reaction mixture was poured into 200 ml of water, extracted with 200 ml of toluene, followed by separation thereof, and the organic phase was washed with water sufficiently, followed by drying over anhydrous magnesium sulfate. After the solvent was distilled off under reduced pressure, the resulting residue was purified by silica gel column chromatography (eluent; toluene: ethyl acetate) to obtain 1.81 g (yield: 82%) of (+)-2-{4-(1-hexyloxyethyl)phenyl}-5-decyloxypyrimidine.

后处理

  1. customto subject to reaction at the same temperature for 2 hours
  2. customAfter completion of the reaction
  3. extractionextracted with 200 ml of toluene
  4. customfollowed by separation
  5. washthe organic phase was washed with water sufficiently
  6. dry with materialby drying over anhydrous magnesium sulfate
  7. distillationAfter the solvent was distilled off under reduced pressure
  8. customthe resulting residue was purified by silica gel column chromatography (eluent; toluene: ethyl acetate)

来源与证据

ORD记录
ord-b893edb234c34782b8663ea06395fd3f
来源数据集
uspto-grants-1995_02
专利号
US05389293

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