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

HRID 1707975

반응식

HRID 1707975 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

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-Methoxy-ethoxymethyl 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.

후처리

  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

출처 및 근거

ORD 기록
ord-8e7df7fc2e1844d0bb1cba6b00ca7c1c
출처 데이터셋
uspto-grants-1994_10
특허 번호
US05356898

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