Tert-Butylamine → 8-bromo-N2-(tert-butyl)quinazoline-2,4-diamine

Participants

Reaction Conditions

Reaction Steps

A microwave vial was charged with 8-bromo-2-chloroquinazolin-4-amine (484a; 0.109 g, 0.422 mmol) and tert-butylamine (Aldrich; 1.33 mL, 12.65 mmol). The slurry was heated to 120° C. in a biotage initiator microwave for 30 min. 0.5 mL NMP was added to give a solution and the reaction was heated to 120° C. in a biotage initiator microwave for 30 min. The reaction was heated to 150° C. in a biotage initiator microwave for 30 min. The reaction was heated to 160° C. in a biotage initiator microwave for 30 min and then was heated to 170° C. in a biotage initiator microwave for 30 min. The reaction was partitioned between water and EtOAc. The organic layer was washed with water 2 times, saturated aqueous NaCl once, and the organics were dried over anhydrous Na2SO4, filtered, and concentrated in vacuo to give 8-bromo-N2-(tert-butyl)quinazoline-2,4-diamine (0.133 g, 0.451 mmol, quant. yield) as a brown foam: 1H NMR (400 MHz, CDCl3) δ ppm 7.87 (1H, dd, J=7.5, 1.3 Hz), 7.48 (1H, d, J=7.8 Hz), 6.92 (1H, t, J=7.8 Hz), 5.27 (2H, br. s.), 5.02 (1H, br. s.), 1.55 (9H, s). m/z (ESI, +ve ion) 295.0/297.0 (M+H)+.

Provenance & Evidence