Phosphorus oxychloride → HCID 89782177, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 8-bromo-3-(tetrahydro-2H-pyran-4-yl)quinazoline-2,4(1H,3H)-dione (515b, 1.67 g, 5.14 mmol), phosphoryl trichloride (4.70 mL, 51.4 mmol), and N-ethyl-N-isopropylpropan-2-amine (3.58 mL, 20.54 mmol) was stirred at 90° C. for 20 h. The reaction mixture was concentrated to give a brown oil. Ice was added until the mixture began to stir, and NaHCO3 was added to the mixture; a brown solid which formed was filtered and washed with water. The solid was dissolved in DCM, placed in a separatory funnel, separated, dried over Na2SO4, and concentrated to give 8-bromo-2-chloro-3-(tetrahydro-2H-pyran-4-yl)quinazolin-4(3H)-one (515c, 1.60 g, 4.66 mmol, 91% yield over two steps) as a brown solid. 1H NMR (400 MHz, CDCl3) δ ppm 1.70 (dd, J=12.23, 2.25 Hz, 2H) 3.00 (qd, J=12.36, 4.79 Hz, 2H) 3.51 (td, J=11.93, 1.76 Hz, 2H) 4.14 (dd, J=11.54, 4.69 Hz, 2H) 5.05-5.19 (m, 1H) 7.33 (t, J=7.92 Hz, 1H) 8.00 (dd, J=7.73, 1.27 Hz, 1H) 8.18 (dd, J=8.02, 1.37 Hz, 1H). MS (ESI, pos. ion) m/z: 343.0/344.9 (M+1).

Provenance & Evidence