Toluene → HCID 89783740, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 2-amino-3-bromo-N-(tetrahydro-2H-pyran-4-yl)benzamide (515a, 1.54 g, 5.15 mmol), bis(trichloromethyl) carbonate (0.764 g, 2.57 mmol), and triethylamine (3.59 mL, 25.7 mmol) in DCM (51.5 mL) was refluxed for 16 h. Toluene (50 mL) was added to the clear solution; this mixture was partially concentrated to remove the DCM. More bis(trichloromethyl) carbonate (0.764 g, 2.57 mmol) was added, and the yellow solution was heated to 90° C. for 1 h. The reaction mixture was concentrated to give 8-bromo-3-(tetrahydro-2H-pyran-4-yl)quinazoline-2,4(1H,3H)-dione (515b) as a light yellow solid. 1H NMR (400 MHz, CDCl3) δ ppm 1.56-1.62 (m, 2H) 2.87 (qd, J=12.39, 4.69 Hz, 2H) 3.52 (td, J=12.03, 1.76 Hz, 2H) 4.10 (dd, J=11.54, 4.69 Hz, 2H) 5.11 (tt, J=12.18, 3.96 Hz, 1H) 7.11 (t, J=8.02 Hz, 1H) 7.79 (dd, J=7.82, 1.17 Hz, 1H) 8.09 (s, 1H) 8.11 (s, 1H). MS (ESI, pos. ion) m/z: 325.0/326.9 (M+1).

Provenance & Evidence