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Morpholine → 4-(5-(4-Fluorobenzyl)-4-(2-morpholinoethyl)thiophen-2-yl)-5-chloro-2-(methylthio)pyrimidine

HRID 2267346
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HRID 2267346 반응식
CS(Cl)(=O)=O.[F:6][C:7]1[CH:30]=[CH:29][C:10]([CH2:11][C:12]2[S:13][C:14]([C:20]3[C:25]([Cl:26])=[CH:24][N:23]=[C:22]([S:27][CH3:28])[N:21]=3)=[CH:15][C:16]=2[CH2:17][CH2:18]O)=[CH:9][CH:8]=1.C(N(C(C)C)CC)(C)C.[NH:40]1[CH2:45][CH2:44][O:43][CH2:42][CH2:41]1>ClCCl.C(#N)C>[F:6][C:7]1[CH:30]=[CH:29][C:10]([CH2:11][C:12]2[S:13][C:14]([C:20]3[C:25]([Cl:26])=[CH:24][N:23]=[C:22]([S:27][CH3:28])[N:21]=3)=[CH:15][C:16]=2[CH2:17][CH2:18][N:40]2[CH2:45][CH2:44][O:43][CH2:42][CH2:41]2)=[CH:9][CH:8]=1
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참가 물질

7

반응물 4

HCID 8083MorpholineHCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 602044632-(2-(4-Fluoro-benzyl)-5-(5-chloro-2-(methylthio)pyrimidin-4-yl)thiophen-3-yl)ethanol

생성물 1

HCID 602044644-(5-(4-Fluorobenzyl)-4-(2-morpholinoethyl)thiophen-2-yl)-5-chloro-2-(methylthio)pyrimidine수율 74.2%

시약·촉매·용매 2

HCID 6342Acetonitrile용매HCID 6344Dichloromethane용매

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온도
0 °C

실험 절차

Methanesulfonyl chloride (59 mg, 0.52 mmol) was added to a mixture of 2-(2-(4-fluoro-benzyl)-5-(5-chloro-2-(methylthio)pyrimidin-4-yl)thiophen-3-yl)ethanol (170 mg, 0.43 mmol) and diisopropylethylamine (72 mg, 0.55 mmol) in dichloromethane (8 mL) at 0° C. After stirring at 0° C. for 1 h, the solvent was removed in vacuo. Acetonitrile (5 mL) and morpholine (112 mg, 1.29 mmol) were added to the residue and the mixture was heated to 70° C. overnight. After cooling to rt solvent was evaporated in vacuo and the product was purified by flash chromatography eluting with methanol (1 M ammonia)/dichloromethane (1:20) to afford the title compound (148 mg, 74%). MS (M+H)+ 464/466.

후처리

  1. customthe solvent was removed in vacuo
  2. temperaturethe mixture was heated to 70° C. overnight
  3. temperatureAfter cooling to rt solvent
  4. customwas evaporated in vacuo
  5. customthe product was purified by flash chromatography
  6. washeluting with methanol (1 M ammonia)/dichloromethane (1:20)

출처 및 근거

ORD 기록
ord-ccab02cf9a8f441e9a4b41250539062e
출처 데이터셋
uspto-grants-2010_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07858785B2

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