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A mixture of 3-amino-isonicotinic acid (32)(26.24 g, 190.0 mmol) and formamidine acetate (39.56 g, 380 mmol) in dimethylacetamide (100 ml) was stirred and heated to 150° C. The reaction was maintained at this temperature with stirring for 12 hours before it was allowed to cool to 25° C. and then basified with sodium bicarbonate solution (5percent aqueous) until pH 7-8 was attained. The resultant pale brown solid was removed by filtration, washed with water (20 ml) and dried in a desiccator to give the desired compound (24.50 g, 87.63percent) which required no further purification. m/z (LC-MS, ESP): 148 [M+H]+, R/T=1.09 mins.
3H-Pyrido[3,4-d]pyrimid-4-one. A mixture of 3-amino isonicotinic acid (485 mg, 3.51 mmol) in formamide (3 mL) is heated to 160° C. for 12 h. Upon cooling, the resulting solid is filtered and washed with H2 O and dried in a vacuum oven to yield 3H-pyrido[3,4-d]pyrimid-4-one (373 mg, 72percent). 1 H NMR (DMSO) delta 12.60 (1H, brs), 9.06 (1H, s), 8.68 (1H, d, J=5.3 Hz), 8.23 (1H, s), 7.96 (1H, d, J=5.1 Hz).
In water; formamide;
Preparation 1 Pyrido[3,4-d]pyrimidin-4(3H)one A mixture of 4 g of 3-amino-pyridine-4-carboxylic acid in 15 mL of formamide was heated in an oil bath to 160-180° C. After one hour the mixture was allowed to cool. Then, the mixture was slurried in 25 mL of water and filtered. The product was recrystallized from water. Yield 3.3 g. M.P. 317° C. (with sublimation).
In ethanol; at 160℃; for 0.5h;Microwave irradiation;
A Biotage microwave vial was charged with 3-aminoisonicotinic acid (691 mg, 5.0 mmol), formamidine acetate (573 mg, 5.5 mmol), and ethanol (10 mL). The reaction mixture was heated in the microwave at 160 °C for 30 min, diluted with H20 (20 mL), and cooled to 0 °C. The suspension was filtered and the solids were washed with cold H20 (10 mL) to provide quinazoline A2 (259 mg, 35percent) as a white solid: LC-MS (>98percent) m/z = 148.0[M+H], Rt= 0.604.
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