Reaction #665896

Reaction equation

phenylboronic acid

tert-butyl (3S)-3-{[8-(aminocarbonyl)-6-iodoquinazolin-4-yl]amino}piperidine-1-carboxylate

cesium carbonate

→

tert-butyl (3S)-3-{[8-(aminocarbonyl)-6-phenylquinazolin-4-yl]amino}piperidine-1-carboxylate

Solvents

THF

Conditions

Workup

1. 1
   TemperatureHeated
2. 2
   Otherreaction in the microwave at 130 deg C
3. 3
   ConcentrationConcentrated
4. 4
   Otherreaction
5. 5
   OtherPurified by silica gel chromatography (Biotage; 10 g column; 15 mL/min; 1-10% MeOH/CH2Cl2)
6. 6
   OtherConcentrated product to give an oil

Procedure

Combined phenylboronic acid (16.18 mg; 0.13 mmol; 1.20 eq.), tert-butyl (3S)-3-{[8-(aminocarbonyl)-6-iodoquinazolin-4-yl]amino}piperidine-1-carboxylate (55.00 mg; 0.11 mmol; 1.00 eq.), and bis(tri-tert-butylphosphoranyl)palladium (5.67 mg; 0.01 mmol; 0.10 eq.) in a microwave tube. Then added THF (0.70 ml) followed by cesium carbonate (0.22 ml; 2.00 M; 0.44 mmol; 4.00 eq.). Heated reaction in the microwave at 130 deg C. for 20 minutes. LCMS: M+1=448 major peak (266 present). Concentrated reaction. Purified by silica gel chromatography (Biotage; 10 g column; 15 mL/min; 1-10% MeOH/CH2Cl2). Concentrated product to give an oil. LCMS: M+1=448 major peak.

Source