4-Benzyloxyaniline → 4-(4-Benzyloxyanilino)pyrido[2,3-d]pyrimidine
Reaction equation
Cl[C:2]1[C:3]2[CH:11]=[CH:10][CH:9]=[N:8][C:4]=2[N:5]=[CH:6][N:7]=1.[CH2:12]([O:19][C:20]1[CH:26]=[CH:25][C:23]([NH2:24])=[CH:22][CH:21]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>C(O)C>[CH2:12]([O:19][C:20]1[CH:21]=[CH:22][C:23]([NH:24][C:2]2[C:3]3[CH:11]=[CH:10][CH:9]=[N:8][C:4]=3[N:5]=[CH:6][N:7]=2)=[CH:25][CH:26]=1)[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
4-Chloropyrido[2,3-d]pyrimidine (prepared as described in: R. K. Robins and G. W. Hitchings, J. Am. Chem. Soc, 77, 2256 (1955)) (0.165 g, 1.0 mmol) and 4-benzyloxyaniline (0.199 g, 1.0 mmol) were reacted in ethanol (10 ml) for ca. 2 hours, according to Procedure A. After cooling, the mixture was filtered, treated with triethylamine and concentrated in vacuo. Purification by column chromatography on silica, eluting with methanol/chloroform (1:10), gave the product as a yellow solid (0.020 g, 6%) with m.p. 235-237° C.; (Found: C, 72.34; H, 4.85; N, 16.57. C20H16N4O0.25H2O requires: C, 72.16; H, 4.99; N, 16.83%); δH [2H6]-DMSO 9.10 (1H, d, J 9) and 9.08 (1H, d, J 5) (6H, 8-H), 8.78 (1H, s, 2-H), 7.76 (1H, dd, J 9, 5, 7-H), 7.62 (2H, d, J 9, 2′-H, 6′-H), 7.43 (2H, d, J 7, 2″-H, 6″-H), 7.38 (2H, t, J 7, 3″-H, 5″-H), 7.30 (1H, t, J 8, 4″-H), 7.08 (2H, d, J 9, 3′-H, 5′-H), 5.11 (2H, s, CH2); m/z (%) 328 (68, M+), 237 (100), 91 (64).