6-Chloropyrido[3,4-d]pyrimidin-4(3H)-one

A mixture of compound 5-amino-2-chloropyridine-4-carboxylic acid(1000 g, 5.8 mol) was dissolved in 5000 mlEthylene glycol monomethyl ether, AddedFormamidine hydrochloride(1867 g, 23.2 mol), sodium acetate (2360 g, 17.4 mol). The reaction was heated to 120 ° C for 6 hours. After the reaction was complete, the reaction was cooled to room temperature, poured into 4000 ml of water and extracted twice with ethyl acetate. The organic phase was combined, dried and concentrated to afford the crude product which was filtered to give 6-chloropyridine And [3, 4-d] pyrimidin-4 (3H) ketone (924 g, 5-1 mol)Step 1: containing 1.3 g of 5-amino-2-chloro nicotinic acid (7.6 mmol) and 0.66 g methyl acyl imide amide (formimidamide) (15.1 mmol, 2.0 equiv.) Of acetic acid was heated to 120 acid to give 6-chloro-pyrrolo for 4 hours, the solvent is removed after the addition of an aqueous solution containing sodium hydrogen carbonate solution is adjusted to a value of 8, filtered, and then [3, 4-d] pyrimidin -4 (3H) - one (1.1 g, yield 81.5percent).Step (e): 6-CHLORO-3H-PYRIDO [3, 4-D] PYRIMIDIN-4-ONE A suspension of 5-amino-2-chloro-isonicotinic acid in formamide (240 mL) was heated at an internal temperature of 140°C overnight with stirring. The mixture was cooled to room temperature, diluted with water (600mL), and stirred for 1 hour. The resulting solid was collected by filtration, washed with water, and dried to give 17. 20g of 6-chloro-3H-pyrido [3, 4-d] PYRIMIDIN-4-ONE as a brown solid (83. 9percent yield). 1H NMR (400 MHz, DMSO-D6) d ppm 7.9 (s, 1H), 8.2 (s, 1H), 8.9 (s, 1H), 12.7 (bs, 1H) MS (APCI) M+1 = 182.0Step (e) 6-Chloro-3H-pyrido [3, 4-d] pyrimidin-4-one A 1 L round bottomed flask was charged with 5-amino-2-chloro- isonicotinic acid (69.5 g, 0.40 moles), formamidine acetate (84 g, 0.81 moles, 2 mole equivalents), and 600 mL of methoxyethanol. The resulting solution was heated at reflux for 18 hours. After cooling to 5°C, a precipitate was collected by filtration, washed twice with methoxyethanol, and dried overnight in the vacuum oven at 45°C. The reaction yielded 67 g (92percent total yield) of 6-chloro-3H- pyrido [3, 4-D] PYRIMIDIN-4-ONE as a tan solid that was sufficiently pure by NMR to use in the next reaction. 8H (DMSO) 12.70 (1 H, s), 8.86 (1 H, d), 8. 19 (1 H, s), 7.93 (1 H, d) MS [M+H3+ 182

Molecular Weight:181.58
XLogP3:0.6
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:3
Exact Mass:181.0042895
Monoisotopic Mass:181.0042895
Topological Polar Surface Area:54.4
Heavy Atom Count:12
Complexity:231
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes