1,2-Dichloroethane → 2-[N,N-bis(tert-butoxycarbonyl)amino]-5-(ter-butyl-dimethyl-silanyloxymethyl)-pyrimidin

Beteiligte Stoffe

Reaktionsbedingungen

Reaktionsschritte

A solution of 2-[N,N-bis(tert-butoxycarbonyl)amino]-5-bromopyrimidin (16.0 g, 45.0 mmol), tert-butyl-dimethyl-tributylstannanylmethoxy-silane (20.5 g, 47.1 mmol), and bis(triphenylphosphine)palladium(II) dichloride (1.00 g, 1.40 mmol) in 1,2-dichloroethane (50 mL) was stirred at reflux overnight. Additional bis(triphenylphosphine)palladium(II) dichloride (1.00 g, 1.40 mmol) was added and the solution was refluxed for 8 h. The mixture was cooled to 0° C. and diethyl ether (200 mL) was added followed by saturated aqueous potassium fluoride (50 mL). The mixture was stirred vigourously for 60 min and filtered. The organic phase was washed with water, dried and concentrated under reduced pressure. Flash chromatography (MeOH/CH2Cl2, 1:99) gave 2-[N,N-bis(tert-butoxycarbonyl)amino]-5-(tert-butyl-dimethyl-silanyloxymethyl)-pyrimidin (10.2 g, 55%).

Herkunft & Nachweise