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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 NaHCO3 solution (5 percent in H2O) (3 volumes) were carefully added and the mixture stirred vigorously. The resulting <n="113"/>precipitate was collected by filtration and then washed with water (2 X 1 volume) and then t- butyl methylether (2 X 1 volume) before being dried in a vacuum oven to give the desired product which required no further purification.6-Bromo-3H-pyrido[2,3-d]pyriniidin-4-one: (91 percent yield, insert) m/z (LC-MS,ESP):225 [M- H]- R/T = 2.31 minutes)
To 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. 1H NMR (300?MHz, DMSO-d6) δ 12.72 (s, 1H), 9.03 (d, J?=?2.4?Hz, 1H), 8.61 (d, J?=?2.4?Hz, 1H), 8.35 (s, 1H); MS (ESI, m/z): 225.8 [M+H]+.
Reference：
[1] Bioorganic and Medicinal Chemistry, 2018, vol. 26, # 8, p. 1713 - 1726
[2] Bioorganic and Medicinal Chemistry, 2012, vol. 20, # 17, p. 5169 - 5180
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[ 3473-63-0 ]
[ 52833-94-0 ]
[ 155690-79-2 ]
Yield
Reaction Conditions
Operation in experiment
1.7 g
at 120℃; for 36 h; Inert atmosphere
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) ? 12.70 (s, 1H), 9.01 (d, J= 2.6 Hz, 1H), 8.59 (d, J= 2.6 Hz, 1H), 8.33 (s, 1H).
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