Sodium methanethiolate → 2-Chloro-4-(methylthio)pyrimidine

HRID 539900

反応式

HRID 539900 の反応式
C([C:3]1[C:4](Cl)=[N:5][C:6]([Cl:9])=[N:7][CH:8]=1)C.[CH3:11][S-:12].[Na+]>O1CCCC1.C(OCC)(=O)C>[Cl:9][C:6]1[N:5]=[C:4]([S:12][CH3:11])[CH:3]=[CH:8][N:7]=1

参加物

5

反応物 2

HCID 4378561Sodium methanethiolateHCID 100124582,4-Dichloro-5-ethylpyrimidine

生成物 1

HCID 164271482-Chloro-4-(methylthio)pyrimidine収率 53.6%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of ethyl 2,4-dichloropyrimidine (20.0 g, 0.13 mol) in 150 mL of anhydrous tetrahydrofurane was added sodium thiomethoxide (49.30 mL, 0.15 mol) at −10° C. The reaction mixture was allowed to warm up to room temperature and then stirred for 5 hours with monitoring a reaction with LC-MS or thin layer chromatography (TLC). The reaction mixture was diluted with ethyl acetate and washed with brine (×2). The collected organic layer was dried over anhydrous sodium sulfate and then concentrated in vacuo. The resulting solid was slurrified with diethyl ether and then collected by filtration to afford the desired intermediate 10 as a white solid (11.2 g, 52%)

後処理

  1. customa reaction with LC-MS or thin layer chromatography (TLC)
  2. washwashed with brine (×2)
  3. dry with materialThe collected organic layer was dried over anhydrous sodium sulfate
  4. concentrationconcentrated in vacuo
  5. filtrationcollected by filtration

出典と根拠

ORDレコード
ord-4f1103dca1964454aec85ad23af160f0
出典データセット
uspto-grants-2014_10
特許番号
US08871778B2

関連ノート

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