Water → HCID 86696695, 화합물

HRID 1774193노트

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HRID 1774193 반응식
[CH3:1][C:2]1[N:7]=[C:6]([NH2:8])[CH:5]=[CH:4][N:3]=1.[Si:9]([O:16][CH2:17][C@@H:18]([N:27]1[CH:32]=[CH:31][C:30]([C:33]2[CH:38]=[CH:37][N:36]=[C:35](S(C)(=O)=O)[N:34]=2)=[CH:29][C:28]1=[O:43])[C:19]1[CH:24]=[CH:23][C:22]([Cl:25])=[C:21]([F:26])[CH:20]=1)([C:12]([CH3:15])([CH3:14])[CH3:13])([CH3:11])[CH3:10].O>C(O)(CC)C>[Si:9]([O:16][CH2:17][C@@H:18]([N:27]1[CH:32]=[CH:31][C:30]([C:33]2[CH:38]=[CH:37][N:36]=[C:35]([NH:8][C:6]3[CH:5]=[CH:4][N:3]=[C:2]([CH3:1])[N:7]=3)[N:34]=2)=[CH:29][C:28]1=[O:43])[C:19]1[CH:24]=[CH:23][C:22]([Cl:25])=[C:21]([F:26])[CH:20]=1)([C:12]([CH3:15])([CH3:13])[CH3:14])([CH3:11])[CH3:10]

참가 물질

5

반응물 3

HCID 962WaterHCID 2957632-Methylpyrimidin-4-amineHCID 71727006(S)-1-(2-((tert-Butyldimethylsilyl)oxy)-1-(4-chloro-3-fluorophenyl)ethyl)-4-(2-(methylsulfonyl)pyrimidin-4-yl)pyridin-2(1H)-one

생성물 1

HCID 86696695HCID 86696695, 화합물수율 32%

시약·촉매·용매 1

HCID 6568(+-)-2-Butanol용매

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온도
110 °C

실험 절차

2-Methylpyrimidin-4-amine (0.41 g, 3.7 mmol) and (S)-1-(2-(tert-butyldimethylsilyloxy)-1-(4-chloro-3-fluorophenyl)ethyl)-4-(2-(methylsulfonyl)pyrimidin-4-yl)pyridin-2(1H)-one (0.10 g, 0.19 mmol) were placed in sec-BuOH (1 mL), heated to 110° C. in a sealed tube for 18 hours, then poured into water, and extracted with DCM. The combined organic fractions were dried (MgSO4), filtered, and concentrated to give the crude product, which was purified by column chromatography (500:5 DCM/MeOH to remove impurity, then 500:15 for product) to give (S)-1-(2-(tert-butyldimethylsilyloxy)-1-(4-chloro-3-fluorophenyl)ethyl)-4-(2-((2-methylpyrimidin-4-yl)amino)pyrimidin-4-yl)pyridin-2(1H)-one (0.034 g, 32% yield).

후처리

  1. extractionextracted with DCM
  2. dry with materialThe combined organic fractions were dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto give the crude product, which
  6. customwas purified by column chromatography (500:5 DCM/MeOH
  7. customto remove impurity

출처 및 근거

ORD 기록
ord-6acd724d87064f98996366e2ee64014e
출처 데이터셋
uspto-grants-2016_02
특허 번호
US09259470B2

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