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

HRID 643510ノート

反応式

HRID 643510 の反応式
[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]

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 67553Tetrabutylammonium Iodide触媒HCID 6228Dimethylformamide溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-54229817b67346babcdf2b28e0f802bb
出典データセット
uspto-grants-2010_04
特許番号
US07700605B2

反応ノート

読み込み中…