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Cesium carbonate → (R)-4-Chloro-6-(1-(4-chloro-2-(3-methyl-1H-pyrazol-1-yl)phenyl)-2,2,2-trifluoroethoxy)pyrimidin-2-amine

HRID 1499150
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HRID 1499150 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([OH:13])[C:9]([F:12])([F:11])[F:10])=[C:4]([N:14]2[CH:18]=[CH:17][C:16]([CH3:19])=[N:15]2)[CH:3]=1.[Cl:20][C:21]1[CH:26]=[C:25](Cl)[N:24]=[C:23]([NH2:28])[N:22]=1.C([O-])([O-])=O.[Cs+].[Cs+]>O1CCOCC1>[Cl:20][C:21]1[CH:26]=[C:25]([O:13][C@H:8]([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][C:4]=2[N:14]2[CH:18]=[CH:17][C:16]([CH3:19])=[N:15]2)[C:9]([F:12])([F:11])[F:10])[N:24]=[C:23]([NH2:28])[N:22]=1
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5

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HCID 10796Cesium carbonateHCID 655222-Amino-4,6-dichloropyrimidineHCID 25210912(alphaR)-4-Chloro-2-(3-methyl-1H-pyrazol-1-yl)-alpha-(trifluoromethyl)benzenemethanol

생성물 1

HCID 117952532(R)-4-Chloro-6-(1-(4-chloro-2-(3-methyl-1H-pyrazol-1-yl)phenyl)-2,2,2-trifluoroethoxy)pyrimidin-2-amine

시약·촉매·용매 1

HCID 312751,4-Dioxane
용매

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온도
80 °C

실험 절차

To a solution of (1R)-1-[4-chloro-2-(3-methylpyrazol-1-yl)phenyl]-2,2,2-trifluoroethanol (40 g, 138 mmol) in dioxane (400 mL) was added 4,6-dichloropyrimidin-2-amine (113 g, 690 mmol) and Cs2CO3 (132 g, 405 mmol). The mixture was heated for 24 h at 80° C. The reaction was then cooled to RT and filtered. The solvent was removed in vacuo, then CH2Cl2 and heptane was added. The solvent volume was reduced until a solid precipitated out. The solid was filtered and the procedure repeated several times to provide 4-chloro-6-[(1R)-1-[4-chloro-2-(3-methylpyrazol-1-yl)phenyl]-2,2,2-trifluoro-ethoxy]pyrimidin-2-amine as a white solid.

후처리

  1. temperatureThe reaction was then cooled to RT
  2. filtrationfiltered
  3. customThe solvent was removed in vacuo
  4. additionCH2Cl2 and heptane was added
  5. customprecipitated out
  6. filtrationThe solid was filtered

출처 및 근거

ORD 기록
ord-9273fb65c94246c393021462c6b6272b
출처 데이터셋
uspto-grants-2015_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09199994B2

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