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

HRID 643510Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 643510
[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]

Komponenten

7

Edukt 4

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 67553Tetrabutylammonium IodideKatalysatorHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-54229817b67346babcdf2b28e0f802bb
Quelldatensatz
uspto-grants-2010_04
Patentnummer
US07700605B2

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