2-(2-Hydroxyethyl)pyridine → 4-Furan-2-yl-6-(2-pyridin-2-yl-ethoxy)-pyrimidin-2-ylamine

HRID 1356073

반응식

HRID 1356073 반응식
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[CH:11]=[C:10](S(C)=O)[N:9]=[C:8]([NH2:15])[N:7]=1.[OH:16][CH2:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=1.C1CCN2C(=NCCC2)CC1>COCCOC>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[CH:11]=[C:10]([O:16][CH2:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=2)[N:9]=[C:8]([NH2:15])[N:7]=1

참가 물질

5

반응물 3

HCID 76752-(2-Hydroxyethyl)pyridineHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 185072094-Furan-2-yl-6-methanesulfinyl-pyrimidin-2-ylamine

생성물 1

HCID 185072124-Furan-2-yl-6-(2-pyridin-2-yl-ethoxy)-pyrimidin-2-ylamine수율 35%

시약·촉매·용매 1

HCID 80711,2-Dimethoxyethane용매

반응 조건

온도
100 °C

실험 절차

To a stirred suspension of 500 mg (2.24 mmol) 4-furan-2-yl-6-methanesulfinyl-pyrimidin-2-yl-amine in 20 ml DME was added 0.50 ml (4.48 mmol) 2-(2-hydroxyethyl)pyridine and 0.84 ml (5.60 mmol) DBU and the mixture heated at 100° C. for 72 hours. The reaction mixture was then cooled to room temperature and partitioned between water and dichloromethane. The organic phase was dried over sodium sulfate and concentrated in vacuo. Chromatography (ethyl acetate) followed by trituration in ether afforded 220 mg (35%) 4-furan-2-yl-6-(2-pyridin-2-yl-ethoxy)-pyrimidin-2-ylamine as a white crystalline solid. ES-MS m/e (%): 283 (M+H+, 100).

후처리

  1. temperatureThe reaction mixture was then cooled to room temperature
  2. custompartitioned between water and dichloromethane
  3. dry with materialThe organic phase was dried over sodium sulfate
  4. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-3dae4ce8c7d947ba905788575a92f4a6
출처 데이터셋
uspto-grants-2003_07
특허 번호
US06586441B2

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