Sodium hydride → 1-(2,6-Dichloro-5-methoxy-pyrimidin-4-yloxy)-cyclopropanecarboxylic acid methyl ester

HRID 528466ノート

反応式

HRID 528466 の反応式
[Cl:1][C:2]1[N:7]=[C:6]([Cl:8])[C:5]([O:9][CH3:10])=[C:4](Cl)[N:3]=1.[CH3:12][O:13][C:14]([C:16]1([OH:19])[CH2:18][CH2:17]1)=[O:15].[H-].[Na+]>C1COCC1>[CH3:12][O:13][C:14]([C:16]1([O:19][C:4]2[C:5]([O:9][CH3:10])=[C:6]([Cl:8])[N:7]=[C:2]([Cl:1])[N:3]=2)[CH2:18][CH2:17]1)=[O:15]

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 2733178Methyl 1-hydroxy-1-cyclopropane carboxylateHCID 202711362,4,6-Trichloro-5-methoxypyrimidine

生成物 1

HCID 867117501-(2,6-Dichloro-5-methoxy-pyrimidin-4-yloxy)-cyclopropanecarboxylic acid methyl ester

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of 2,4,6-trichloro-5-methoxy-pyrimidine (213 mg, 1.00 mmol) and 1-hydroxy-cyclopropanecarboxylic acid methyl ester (139 mg, 1.20 mmol) in THF (4 mL) was added sodium hydride (48 mg, 1.20 mmol, 60% dispersion in mineral oil) at −78° C. The resulting mixture was allowed to warm to RT and stirred for 2 hours. The reaction mixture was quenched with saturated aqueous ammonium chloride solution and extracted with ethyl acetate. The combined organic extracts were dried (Na2SO4) and concentrated in vacuo affording 1-(2,6-Dichloro-5-methoxy-pyrimidin-4-yloxy)-cyclopropanecarboxylic acid methyl ester as a white solid (300 mg, quantitative). LCMS: RT=3.49 min, [M+H]+=341/343/345.

後処理

  1. customThe reaction mixture was quenched with saturated aqueous ammonium chloride solution
  2. extractionextracted with ethyl acetate
  3. dry with materialThe combined organic extracts were dried (Na2SO4)
  4. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-cc0307f8270d43adaf7f97e0979f4e12
出典データセット
uspto-grants-2016_05
特許番号
US09346817B2

反応ノート

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