반응 #730693

반응 방정식

DABCO

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

DABCO

KCN

EtOAc

→

title compound

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

용매

DMSO water

반응 조건

후처리

1. 1
   기타is continued for a total of 1 h 50 min
2. 2
   workup.ADDITIONThe reaction mixture is poured onto brine
3. 3
   세척washed with water and brine
4. 4
   건조dried (Na2SO4)
5. 5
   여과After filtration
6. 6
   기타the solvent is removed under reduced pressure
7. 7
   기타the crude product is purified by flash chromatography over silica gel (eluting with Hexane/EtOAc 80:20)

실험 절차

{4-[3-(2-Chloro-pyrimidin-4-yloxy)-phenoxymethyl]-benzyl}carbamic acid tert-butyl ester (126 mg; 0.285 mmol; Stage 5.2), DABCO (16 mg; 0.143 mmol) and KCN (38 mg; 0.584 mmol) are dissolved in DMSO/water 4:1 (4 mL) at rt under an atmosphere of argon. After 20 min, more DABCO (16 mg) is added and the reaction is continued for a total of 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 5.3 as an oil; ES-MS: [M−H]−; m/z=431; Rf (Hexane/EtOAc 1:1)=0.45; HPLC: AtRet=5.19 min.

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