1,2-Dimethoxyethane → 4-Chloro-5-ethyl-6-(furan-2-yl)-pyrimidine

HRID 1527640노트

반응식

HRID 1527640 반응식
[Cl:1][C:2]1[C:7]([CH2:8][CH3:9])=[C:6](Cl)[N:5]=[CH:4][N:3]=1.[O:11]1[CH:15]=[CH:14][CH:13]=[C:12]1B(O)O.C(COC)OC.C(=O)([O-])[O-].[Na+].[Na+]>O>[Cl:1][C:2]1[C:7]([CH2:8][CH3:9])=[C:6]([C:12]2[O:11][CH:15]=[CH:14][CH:13]=2)[N:5]=[CH:4][N:3]=1

참가 물질

6

반응물 4

HCID 80711,2-DimethoxyethaneHCID 10340Sodium CarbonateHCID 2734357Furan-2-boronic acidHCID 218284324,6-Dichloro-5-ethylpyrimidine

생성물 1

HCID 656454164-Chloro-5-ethyl-6-(furan-2-yl)-pyrimidine수율 51.4%

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
80 °C

실험 절차

A mixture of 4,6-dichloro-5-ethylpyrimidine (10 g), 2-furylboronic acid (6.33 g) tetrakis(triphenylphosphine)palladium (1.94 g), dimethoxyethane (100 ml), and sodium carbonate solution (2 mol/l) (60 ml) was stirred at 70° C. for 2 hours and at 80° C. for 2 hours. After standing to cool the reaction mixture to room temperature, to the reaction mixture, water was added, and extracted with ethyl acetate. The organic layer was dried over sodium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 6.06 g of 4-chloro-5-ethyl-6-(furan-2-yl)-pyrimidine.

후처리

  1. temperatureto cool the reaction mixture to room temperature
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-96d52de5ab5e426297f083d43a7a73b9
출처 데이터셋
uspto-grants-2015_07
특허 번호
US09089136B2

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