Sodium hydride → 4,6-Ditert-butyl-5-[(2-methoxyethoxy)methoxy]-2-methylpyrimidine

HRID 6342

反応式

HRID 6342 の反応式
[CH3:1][C:2]([C:5]1[C:10]([OH:11])=[C:9]([C:12]([CH3:15])([CH3:14])[CH3:13])[N:8]=[C:7]([CH3:16])[N:6]=1)([CH3:4])[CH3:3].[H-].[Na+].[CH3:19][O:20][CH2:21][CH2:22][O:23][CH2:24]Cl>O1CCCC1>[CH3:4][C:2]([C:5]1[C:10]([O:11][CH2:19][O:20][CH2:21][CH2:22][O:23][CH3:24])=[C:9]([C:12]([CH3:15])([CH3:14])[CH3:13])[N:8]=[C:7]([CH3:16])[N:6]=1)([CH3:1])[CH3:3]

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 775901-(Chloromethoxy)-2-methoxyethaneHCID 98778664,6-Bis(1,1-dimethylethyl)-5-hydroxy 2-methylpyrimidine

生成物 1

HCID 199229904,6-Ditert-butyl-5-[(2-methoxyethoxy)methoxy]-2-methylpyrimidine

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

4,6-Bis(1,1-dimethylethyl) 5 hydroxy-2-methyl pyrimidine (9.8 g, 44.1 mmoles) is dissolved in 100 mL of tetrahydrofuran and added dropwise to a suspension of sodium hydride (1.2 g, 48.5 mmoles) in THF (50 mL) at 0° C. The reaction mixture is warmed to room temperature over 15 minutes. 2-Methoxyethoxymethyl chloride (7.1 g, 57.3 mmoles) is added to the reaction mixture at room temperature. After being stirred at room temperature for 4 hours, the reaction is quenched by the addition of saturated ammonium chloride and the tetrahydrofuran is evaporated. The organics are extracted into 300 mL of ether. The ether is washed with 100 mL of brine and dried over magnesium sulfate. Evaporation of the solvent gives the crude product which is purified by flash chromatography (silica, 10% ether/hexane). Yield of 4,6 bis(1,1-dimethylethyl)-5-[(2-methoxyethoxy)methoxy]-2-methylpyrimidine=11.3 g (82%) as a clear oil.

後処理

  1. customthe reaction is quenched by the addition of saturated ammonium chloride
  2. customthe tetrahydrofuran is evaporated
  3. extractionThe organics are extracted into 300 mL of ether
  4. washThe ether is washed with 100 mL of brine
  5. dry with materialdried over magnesium sulfate
  6. customEvaporation of the solvent

出典と根拠

ORDレコード
ord-9502ecdb7f4d41659d2e170dd6a9e06b
出典データセット
uspto-grants-1993_09
特許番号
US05248682

関連ノート

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