8-BROMO-2,4-DICHLOROQUINAZOLINE

To a flask charged with 8-bromoquinazoline-2, 4-diol 2 (39.61 g, 164 mmol) was added PCICompound 19-f (5.5 g, 22.9 mmol) was dissolved in phosphorus oxychloride (30 mL), N, N-dimethylaniline (5mL) was added and the reaction mixture was heated at 110°C for 18 hours. The reaction mixture was cooled to roomtemperature, the reaction mixture was concentrated under reduced pressure to remove phosphorus oxychloride. Theresidue was concentrated and dried. The residue was dissolved with dichloromethane (500 mL) and washed with water(500 mL). The separated organic phase was dried over anhydrous sodium sulfate, filtered, and the filtrate was concentratedunder reduced pressure. The residue was purified by silica gel column chromatography (petroleum ether: dichloromethane= 3: 1) to deliver a pale yellow solid 19-e (2.5 g, yield: 40percent). LC-MS (ESI): m/z = 277 [M+H]+.Compound 44-f (5.5 g, 22.9 mmol) was dissolved in phosphorus oxychloride (30 mL), N, N-dimethylaniline (5 mL) was added and the reaction solution was heated at 110° C. for 18 hours. The reaction was cooled to room temperature and concentrated under reduced pressure to remove phosphorus oxychloride. The residue was concentrated to dryness and the residue was dissolved in dichloromethane (500 mL) and washed with water (500 mL). The separated organic phase was dried over anhydrous sodium sulfate, filtered and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (petroleum ether: dichloromethane=3:1) to give 44-e as a pale yellow solid (2.5 g, yield 40percent). LC-MS (ESI): m/z=277[M+H]To a mixture of 8-bromoquinazoline-2, 4(lH, 3H)-dione (12.1 g, 50 mmol, 1 eq.) in POCl[0287] To a mixture of 8-bromoquinazoline-2, 4(1H, 3H)-dione (12.1 g, 50 mmol, 1 eq.) in POC13 (130 mL) was added DMF (0.5 mL). The mixture was stirred at 130 °C for 12 h, then cooled to r.t. and concentrated. The resulting residue was dissolved in EA (100 mL) and poured into ice-water with vigorous stirring. The organic phase was separated and washed with brine, dried over anhydrous Na2 SO4 and concentrated. The resulting residue was purified via column chromatography (PE/EA==10:1, v/v) to afford 8-bromo-2, 4- dichloroquinazoline as a yellow solid (9.1 g, 60percent yield).

Molecular Weight:277.93
XLogP3:4.2
Hydrogen Bond Acceptor Count:2
Exact Mass:275.88567
Monoisotopic Mass:275.88567
Topological Polar Surface Area:25.8
Heavy Atom Count:13
Complexity:193
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes