p-Toluenesulfonic acid → HCID 117775045, compound

Reaction equation

[NH2:1][C:2]1[N:10]=[C:9]([Cl:11])[CH:8]=[CH:7][C:3]=1[C:4]([NH2:6])=[O:5].[F:12][C:13]1[CH:14]=[C:15]([CH:18]=[CH:19][CH:20]=1)[CH:16]=O.CC1C=CC(S(O)(=O)=O)=CC=1>CCO>[Cl:11][C:9]1[CH:8]=[CH:7][C:3]2[C:4](=[O:5])[NH:6][CH:16]([C:15]3[CH:18]=[CH:19][CH:20]=[C:13]([F:12])[CH:14]=3)[NH:1][C:2]=2[N:10]=1

Participants

Procedure

To a solution of 2-amino-6-chloronicotinamide (200 mg, 1.17 mmol) and 3-fluorobenzaldehyde (160 mg, 1.29 mmol) in 20 mL of EtOH was added PTSA (20 mg, 0.12 mmol), and then the mixture was heated at reflux for 16 h. The solution was cooled to room temperature and filtered to give the product of 7-chloro-2-(3-fluorophenyl)-2,3-dihydropyrido[2,3-d]pyrimidin-4(1H)-one (170 mg, yield: 52%) without further purification. 1H-NMR (CDCl3, 400 MHz) δ 8.09 (d, J=8.0 Hz, 1H), 7.41˜7.44 (m, 1H), 7.29˜7.36 (m, 2H), 7.15˜7.19 (m, 1H), 6.84 (d, J=8.0 Hz, 1H), 6.03 (s, 1H), 5.75 (s, 1H), 5.35 (s, 1H). MS (M+H)+: 278/280.