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

HRID 1938109

反応式

HRID 1938109 の反応式
CN(C)C=O.[OH:6][CH:7]([C:9]1[CH:14]=[CH:13][C:12]([C:15]2[N:20]=[CH:19][C:18]([O:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])=[CH:17][N:16]=2)=[CH:11][CH:10]=1)[CH3:8].[H-].[Na+].[C:34]1(C)[CH:39]=[CH:38][C:37](S(OCCCCCC)(=O)=O)=[CH:36][CH:35]=1>O>[CH2:38]([O:6][CH:7]([C:9]1[CH:10]=[CH:11][C:12]([C:15]2[N:20]=[CH:19][C:18]([O:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])=[CH:17][N:16]=2)=[CH:13][CH:14]=1)[CH3:8])[CH2:39][CH2:34][CH2:35][CH2:36][CH3:37]

参加物

6

反応物 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 220448Hexyl p-ToluenesulfonateHCID 214682802-(4-(1-Hydroxyethyl)phenyl)-5-decyloxypyrimidine

生成物 1

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

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
40 °C

実験手順

Into 20 ml of anhydrous dimethylformamide 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.

後処理

  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)

出典と根拠

ORDレコード
ord-26fb137cf1d54cb282a2696069570b59
出典データセット
uspto-grants-1997_12
特許番号
US05693251

関連ノート

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