Tert-Butylamine → 8-bromo-2-(tert-butylamino)-3-(3-((tert-butyldimethylsilyl)oxy)propyl)quinazolin-4(3H)-one

Participants

Reaction Conditions

Reaction Steps

A solution of 8-bromo-3-(3-((tert-butyldimethylsilyl)oxy)propyl)-2-chloroquinazolin-4(3H)-one (500a; 0.080 g, 0.185 mmol) in tert-butylamine (Aldrich; 0.584 mL, 5.56 mmol) was sealed and heated in a biotage initiator microwave at 100° C. for 30 min, 130° C. for 30 min, and 150° C. for 60 min. The reaction was partitioned between satd aq sodium bicarbonate and DCM. The aqueous layer was extracted with DCM 3 times, and the combined organics were dried over anhydrous Na2SO4, filtered, and concentrated in vacuo to give 8-bromo-2-(tert-butylamino)-3-(3-((tert-butyldimethylsilyl)oxy)propyl)quinazolin-4(3H)-one (0.077 g, 0.164 mmol, 89% yield) as a yellow oil. 1H NMR (400 MHz, CDCl3) δ ppm 8.05 (1H, dd, J=8.0, 1.4 Hz), 7.85 (1H, dd, J=7.6, 1.4 Hz), 6.97 (1H, t, J=7.8 Hz), 5.24 (1H, s), 4.10 (2H, t, J=7.1 Hz), 3.75 (2H, t, J=5.4 Hz), 1.85-1.99 (2H, m), 1.62 (9H, s), 0.95 (9H, s), 0.12 (6H, br. s.). m/z (ESI, +ve ion) 468.0/470.0 (M+H)+.

Provenance & Evidence