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Sodium hydride → 4,6-Bis-(1,1-dimethylethyl)-5-[(2-methoxyethoxy) methoxy]-2-pyrimidine carboxylic acid methyl ester

HRID 2226426
ノート
印刷プレビュー

反応式

HRID 2226426 の反応式
[CH3:1][O:2][C:3]([C:5]1[N:10]=[C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])[C:8]([OH:15])=[C:7]([C:16]([CH3:19])([CH3:18])[CH3:17])[N:6]=1)=[O:4].[H-].[Na+].[CH3:22][O:23][CH2:24][CH2:25][O:26][CH2:27]Cl>C1COCC1.O.[NH4+].[Cl-]>[CH3:1][O:2][C:3]([C:5]1[N:6]=[C:7]([C:16]([CH3:19])([CH3:18])[CH3:17])[C:8]([O:15][CH2:22][O:23][CH2:24][CH2:25][O:26][CH3:27])=[C:9]([C:11]([CH3:12])([CH3:13])[CH3:14])[N:10]=1)=[O:4]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 3

HCID 24758Sodium hydrideHCID 775901-(Chloromethoxy)-2-methoxyethaneHCID 152753194,6-Bis (1,1-dimethylethyl)-5-hydroxy-2-pyrimidine carboxylic acid methyl ester

生成物 1

HCID 540881314,6-Bis-(1,1-dimethylethyl)-5-[(2-methoxyethoxy) methoxy]-2-pyrimidine carboxylic acid methyl ester収率 100%

試薬・触媒・溶媒 3

HCID 962Water溶媒
HCID 8028Tetrahydrofuran溶媒2 回
HCID 25517Ammonium Chloride溶媒

反応条件

温度
0 °C

実験手順

A solution of 4,6-bis-(1,1-dimethylethyl)-5-hydroxy-2-pyrimidine carboxylic acid methyl ester (4.0 g, 15.0 mmoles) in 50 mL of THF is added to a suspension of NaH (0.39 g, 16.5 mmoles) in THF (50 mL) at 0° C. When addition is complete, the reaction mixture is stirred at 0° C. for 15 minutes. 2-methoxyethoxymethyl chloride (2.0 g, 16.5 mmoles) is added and the solution is warmed to room temperature. The reaction mixture is stirred at room temperature overnight. It is diluted with 100 mL H2O and 100 mL of saturated aqueous NH4Cl. The layers are separated, and the aqueous phase is washed with Et2O (3×100 mL). The combined organic phases are washed with 100 mL brine and dried over MgSO4. Evaporation of Et2O gives 5.3 g (100%) of the desired ester as an oil.

後処理

  1. additionWhen addition
  2. temperaturethe solution is warmed to room temperature
  3. stirringThe reaction mixture is stirred at room temperature overnight
  4. customThe layers are separated
  5. washthe aqueous phase is washed with Et2O (3×100 mL)
  6. washThe combined organic phases are washed with 100 mL brine
  7. dry with materialdried over MgSO4
  8. customEvaporation of Et2O

出典と根拠

ORDレコード
ord-7303130ac0bd43f19cb4a43613937111
出典データセット
uspto-grants-1994_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05348957

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート