Reaktion #1108457

Reaktionsgleichung

TBAF THF

5-[3-({[tert-Butyl(dimethyl)silyl]oxy}methyl)-2-fluorophenyl]-2-chloropyrimidine

NaH

1-[4-(Hydroxymethyl)piperidin-1-yl]ethan-1-one

→

1-{4-[({5-[2-fluoro-3-(hydroxymethyl)phenyl]pyrimidin-2-yl}oxy)methyl]piperidin-1-yl}ethan-1-one

Ausbeute 82.0%

Lösungsmittel

EtOAc

Water

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGby stirring at room temperature for 1 hour
2. 2
   workup.STIRRINGby stirring at room temperature
3. 3
   Einengenthe organic layer was concentrated under reduced pressure
4. 4
   SonstigeThe obtained residue was purified by silica gel column chromatography (hexane/EtOAc/CHCl3/MeOH)

Vorschrift

1-[4-(Hydroxymethyl)piperidin-1-yl]ethan-1-one (200 mg) and THF (4 ml) were mixed, and NaH (70 mg) was added thereto, followed by stirring at room temperature for minutes. 5-[3-({[tert-Butyl(dimethyl)silyl]oxy}methyl)-2-fluorophenyl]-2-chloropyrimidine (200 mg) was added to the reaction mixture, followed by stirring at room temperature for 1 hour, and then 1 M TBAF/THF (1.2 ml) was added thereto, followed by stirring at room temperature. Water and EtOAc were added to the reaction mixture, and the organic layer was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane/EtOAc/CHCl3/MeOH) to obtain 1-{4-[({5-[2-fluoro-3-(hydroxymethyl)phenyl]pyrimidin-2-yl}oxy)methyl]piperidin-1-yl}ethan-1-one (167 mg).

Quelle