7-BROMOQUINAZOLINE-2,4(1H,3H)-DIONE

Synthesis of 2, 4-dichloro-7-morpholin-4-ylquinazoline 87.0 g (1.33 mol) of sodium cyanate were added to 269.0 g (1.17 mol) of methyl 2-amino-4-bromobenzoate in 1.2 l of acetic acid with stirring at room temperature, and the mixture was subsequently stirred for a further 22 h. The reaction mixture was diluted with 1.5 l of water, and the residue was filtered off with suction. 0.42 l of sodium hydroxide solution (32percent) was added to the solid, the mixture was diluted with 3.5 l of water and heated on a steam bath for 4 h. After cooling, the solid residue was filtered off with suction. Conventional work-up gave 205.2 g of 7-bromo-1H-benzo[d]-1, 3-oxazine-2, 4-dione; HPLC/MS (M+H)Step 4: 7-Bromo-lH-quinazoline-2, 4-dioneTo a 250 mL round bottom flask, 2-amino-4-bromo-benzoic acid (10 g, 0.0463 mol) and urea (27.78 g, 0.4629 mol) were added. The reaction mixture was stirred at 195 °C for 3 h. The reaction mixture was allowed to reach 80 °C and water was added. The aqueous reaction mixture was stirred at 80 °C for 5-10 min then allowed to reach room temperature. The solid was filtered, dried and azeotroped with toluene to afford the title compound [10 g, 90percent]. This material was taken to the next step without any further purification.To a 250 mL round bottom flask, 2-amino-4-bromo-benzoic acid (10 g, 0.0463 mol) and urea (27.78 g, 0.4629 mol) were added. The reaction mixture was stirred at 195° C. for 3 hours. The reaction mixture was allowed to cool to 80° C. and water was added. The aqueous reaction mixture was stirred at 80° C. for 5-10 minutes then allowed to reach room temperature. The solid was filtered, dried and azeotroped with toluene to afford the title compound (10 g, 90percent). This material was taken to the next step without further purification.Under nitrogen protection, 2-pyridine boronic acid (1.2 eq.) was added to a three-necked flask containing 7-bromoquinazoline-(2, 4)dione (24 g, 100 mmol).Potassium carbonate 2eq, Pd(Pph3)4 (1%), Toluene 300ml + ethanol 50ml + 50ml water, Turn on the agitation, Heated to reflux, Reaction for 6 h.The reaction solution was cooled and added with water and ethyl acetate.Concentrated petroleum ether washed brown solid M6 (16.2, 67.8%)

Molecular Weight:241.04
XLogP3:1.5
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:2
Exact Mass:239.95344
Monoisotopic Mass:239.95344
Topological Polar Surface Area:58.2
Heavy Atom Count:13
Complexity:257
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes