Epichlorohydrin → [2-(2-Fluoro-4-trifluoromethyl-phenyl)-ethyl]-[2-methoxy-6-(3-oxiranylmethoxy-phenyl)-pyrimidin-4-yl]-amine

HRID 2110726

반응식

HRID 2110726 반응식
[F:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[CH:4][C:3]=1[CH2:12][CH2:13][NH:14][C:15]1[N:20]=[C:19]([O:21][CH3:22])[N:18]=[C:17]([C:23]2[CH:24]=[C:25]([OH:29])[CH:26]=[CH:27][CH:28]=2)[CH:16]=1.C([O-])([O-])=O.[Cs+].[Cs+].[CH2:36]([CH:38]1[O:40][CH2:39]1)Cl>CN(C=O)C.O>[F:1][C:2]1[CH:7]=[C:6]([C:8]([F:9])([F:10])[F:11])[CH:5]=[CH:4][C:3]=1[CH2:12][CH2:13][NH:14][C:15]1[CH:16]=[C:17]([C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([O:29][CH2:36][CH:38]3[CH2:39][O:40]3)[CH:24]=2)[N:18]=[C:19]([O:21][CH3:22])[N:20]=1

참가 물질

6

반응물 3

HCID 7835EpichlorohydrinHCID 10796Cesium carbonateHCID 690695663-{6-[2-(2-Fluoro-4-trifluoromethyl-phenyl)-ethylamino]-2-methoxy-pyrimidin-4-yl}-phenol

생성물 1

HCID 11705324[2-(2-Fluoro-4-trifluoromethyl-phenyl)-ethyl]-[2-methoxy-6-(3-oxiranylmethoxy-phenyl)-pyrimidin-4-yl]-amine수율 50.8%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

To a suspension of 3-{6-[2-(2-fluoro-4-trifluoromethyl-phenyl)-ethylamino]-2-methoxy-pyrimidin-4-yl}-phenol (280 mg, 0.68 mmol), and Cs2CO3 (0.44 g, 1.36 mmol) in DMF (2 mL) is added epichlorohydrin (80 μL, 1.02 mmol) at room temperature. After 4 h at 20° C., the mixture is diluted with water (10 mL), and extracted with EtOAc (2×10 mL). The extracts are washed with water (2×20 mL), dried (MgSO4), filtered, and concentrated. The residue is chromatographed on SiO2 eluting with 50%EtOAc in heptane to afford [2-(2-fluoro-4-trifluoromethyl-phenyl)-ethyl]-[2-methoxy-6-(3-oxiranylmethoxy-phenyl)-pyrimidin-4-yl]-amine [0.16 g, Example 66]. LCMS: RT=2.62 minutes; MS: 464 (M+H).

후처리

  1. extractionextracted with EtOAc (2×10 mL)
  2. washThe extracts are washed with water (2×20 mL)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue is chromatographed on SiO2 eluting with 50%EtOAc in heptane

출처 및 근거

ORD 기록
ord-1c31fc8caa0042969eb1301943c5093a
출처 데이터셋
uspto-grants-2009_04
특허 번호
US07517889B2

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