Ethyl Acetate → {4-[3-(2-Chloro-pyrimidin-4-yloxy)-phenoxymethyl]-benzyl}carbamic acid tert-butyl ester

HRID 643510노트

반응식

HRID 643510 반응식
[Cl:1][C:2]1[N:7]=[C:6]([O:8][C:9]2[CH:10]=[C:11]([OH:15])[CH:12]=[CH:13][CH:14]=2)[CH:5]=[CH:4][N:3]=1.C([O-])([O-])=O.[Cs+].[Cs+].[C:22]([O:26][C:27](=[O:38])[NH:28][CH2:29][C:30]1[CH:35]=[CH:34][C:33]([CH2:36]Cl)=[CH:32][CH:31]=1)([CH3:25])([CH3:24])[CH3:23].CCOC(C)=O>CN(C=O)C.[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[C:22]([O:26][C:27](=[O:38])[NH:28][CH2:29][C:30]1[CH:31]=[CH:32][C:33]([CH2:36][O:15][C:11]2[CH:12]=[CH:13][CH:14]=[C:9]([O:8][C:6]3[CH:5]=[CH:4][N:3]=[C:2]([Cl:1])[N:7]=3)[CH:10]=2)=[CH:34][CH:35]=1)([CH3:25])([CH3:24])[CH3:23]

참가 물질

7

반응물 4

HCID 8857Ethyl AcetateHCID 10796Cesium carbonateHCID 21194243tert-Butyl 4-(chloromethyl)benzylcarbamateHCID 714221433-((2-Chloropyrimidin-4-yl)oxy)phenol

생성물 1

HCID 86622897{4-[3-(2-Chloro-pyrimidin-4-yloxy)-phenoxymethyl]-benzyl}carbamic acid tert-butyl ester

시약·촉매·용매 2

HCID 67553Tetrabutylammonium Iodide촉매HCID 6228Dimethylformamide용매

실험 절차

Under an atmosphere of argon, 3-(2-chloro-pyrimidin-4-yloxy)-phenol (177 mg; 0.8 mmol; Stage 5.1) is dissolved in DMF (4 mL), followed by addition of Cs2CO3 (1.30 g; 4.0 mmol) and stirring is continued for 20 min. (4-Chloromethyl-benzyl) -carbamic acid tert-butyl ester (203 mg; 0.8 mmol) and tetrabutyl ammonium iodide (20 mg) are added, and the reaction is continued for another 1 h 50 min. The reaction mixture is poured onto brine, taken up into EtOAc, washed with water and brine and dried (Na2SO4). After filtration, the solvent is removed under reduced pressure and the crude product is purified by flash chromatography over silica gel (eluting with Hexane/EtOAc 80:20) to give the title compound of Stage 5.2 as an oil; ES-MS: [M+H]+; m/z=442; Rf (Hexane/EtOAc 1:1)=0.50; HPLC: AtRet=5.29 min.

후처리

  1. waitthe reaction is continued for another 1 h 50 min
  2. additionThe reaction mixture is poured onto brine
  3. washwashed with water and brine
  4. dry with materialdried (Na2SO4)
  5. filtrationAfter filtration
  6. customthe solvent is removed under reduced pressure
  7. customthe crude product is purified by flash chromatography over silica gel (eluting with Hexane/EtOAc 80:20)

출처 및 근거

ORD 기록
ord-54229817b67346babcdf2b28e0f802bb
출처 데이터셋
uspto-grants-2010_04
특허 번호
US07700605B2

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