6-BROMOPYRIDO[2,3-D]PYRIMIDIN-4(1H)-ONE

To a 1.2 M solution of 5-bromoanthranilic acid (1 equiv) in N, N-dimethylformamide was added formamidine acetate (1 equiv). The mixture was heated to reflux and stirred at this temperature for 16 hours. After this time, the reaction was cooled and NaHCOTo a vial was charged with 2-amino-5-bromonicotinic acid 8 (1 g, 4.61 mmol) and 1.1 ml of formamide. The vial was capped and heated at 150 °C for 30 min under microwave irradiation. To the reaction mixture was added water. The precipitate was filtered off and recrystallized from water to afford brown solid in 36percent yield. 2-Amino-S -bromonictoinic acid (2 g) and formamidine acetate (3.0 g) were heated at 120 °C in2-methoxyethanol (15 ml) for 36 h under argon. The heterogeneous reaction mixture was diluted with water and filtered. The solid was suction dried to obtain 1.7 g of 6-bromopyrido[2, 3- d]pyrimidin-4(3H)-one. ‘H NMR (300 MHz, DMSO-d6) ö 12.70 (s, 1H), 9.01 (d, J= 2.6 Hz, 1H), 8.59 (d, J= 2.6 Hz, 1H), 8.33 (s, 1H).To a 1.2 M solution of 5-bromoanthranilic acid (1 equiv) in N, N-dimethylformamide was added formamidine acetate (1 equiv). The mixture was heated to reflux and stirred at this temperature for 16 hours. After this time, the reaction was cooled and NaHCOTo a vial was charged with 2-amino-5-bromonicotinic acid 8 (1 g, 4.61 mmol) and 1.1 ml of formamide. The vial was capped and heated at 150 °C for 30 min under microwave irradiation. To the reaction mixture was added water. The precipitate was filtered off and recrystallized from water to afford brown solid in 36percent yield. 2-Amino-S -bromonictoinic acid (2 g) and formamidine acetate (3.0 g) were heated at 120 °C in2-methoxyethanol (15 ml) for 36 h under argon. The heterogeneous reaction mixture was diluted with water and filtered. The solid was suction dried to obtain 1.7 g of 6-bromopyrido[2, 3- d]pyrimidin-4(3H)-one. ‘H NMR (300 MHz, DMSO-d6) ö 12.70 (s, 1H), 9.01 (d, J= 2.6 Hz, 1H), 8.59 (d, J= 2.6 Hz, 1H), 8.33 (s, 1H).

Molecular Weight:226.03
XLogP3:0.7
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:3
Exact Mass:224.95377
Monoisotopic Mass:224.95377
Topological Polar Surface Area:54.4
Heavy Atom Count:12
Complexity:231
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes