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

HRID 539900

반응식

HRID 539900 반응식
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

참가 물질

5

반응물 2

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

생성물 1

HCID 164271482-Chloro-4-(methylthio)pyrimidine수율 53.6%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

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%)

후처리

  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

출처 및 근거

ORD 기록
ord-4f1103dca1964454aec85ad23af160f0
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08871778B2

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