Sodium hydride → 7-Bromo-4-[1-(3-isopropyl-[1,2,4]oxadiazol-5-yl)-piperidin-4-yloxy]-thieno[3,2-d]pyrimidine

HRID 532495

반응식

HRID 532495 반응식
[CH:1]([C:4]1[N:8]=[C:7]([N:9]2[CH2:14][CH2:13][CH:12]([OH:15])[CH2:11][CH2:10]2)[O:6][N:5]=1)([CH3:3])[CH3:2].[H-].[Na+].[Br:18][C:19]1[C:23]2[N:24]=[CH:25][N:26]=[C:27](Cl)[C:22]=2[S:21][CH:20]=1.[Cl-].[NH4+]>CN(C)C=O>[Br:18][C:19]1[C:23]2[N:24]=[CH:25][N:26]=[C:27]([O:15][CH:12]3[CH2:11][CH2:10][N:9]([C:7]4[O:6][N:5]=[C:4]([CH:1]([CH3:3])[CH3:2])[N:8]=4)[CH2:14][CH2:13]3)[C:22]=2[S:21][CH:20]=1

참가 물질

6

반응물 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 166552667-Bromo-4-chlorothieno[3,2-d]pyrimidineHCID 218977441-(3-Isopropyl-1,2,4-oxadiazol-5-YL)piperidin-4-OL

생성물 1

HCID 682993337-Bromo-4-[1-(3-isopropyl-[1,2,4]oxadiazol-5-yl)-piperidin-4-yloxy]-thieno[3,2-d]pyrimidine수율 83%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
0 °C

실험 절차

30 mg of 1-(3-isopropyl-1,2,4-oxadiazol-5-yl)piperidin-4-ol was dissolved in 2 ml of N,N-dimethylformamide and cooled to 0° C. 9 mg of NaH was added to the mixture and stirred for 30 min. 50 mg of 7-bromo-4-chloro-thieno[3,2-d]pyrimidine was added to the mixture, heated to room temperature and stirred for 2 hr. The resulting mixture was added with aqueous ammonium chloride and extracted twice with ethyl acetate. The organic layer was washed with water, dried over anhydrous sodium sulfate, and concentrated under a reduced pressure to obtain a bubble residue. The resulting residue was crystallized in diethylether solvent to obtain 50 mg of the title compound as a white solid.

후처리

  1. temperatureheated to room temperature
  2. stirringstirred for 2 hr
  3. extractionextracted twice with ethyl acetate
  4. washThe organic layer was washed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under a reduced pressure
  7. customto obtain a bubble residue
  8. customThe resulting residue was crystallized in diethylether solvent

출처 및 근거

ORD 기록
ord-d111b98d2e904b31a5c0bf3133ccae42
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08853213B2

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