4-Benzyloxyaniline → 4-(4-Benzyloxyanilino)pyrido[2,3-d]pyrimidine

HRID 564780

Reaction equation

HRID 564780 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]=1

Participants

4

Reactant 2

HCID 228604-BenzyloxyanilineHCID 5690394-Chloropyrido[2,3-d]pyrimidine

Product 1

HCID 221128934-(4-Benzyloxyanilino)pyrido[2,3-d]pyrimidineYield 6.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

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).

Workup

  1. temperatureAfter cooling
  2. filtrationthe mixture was filtered
  3. additiontreated with triethylamine
  4. concentrationconcentrated in vacuo
  5. customPurification by column chromatography on silica
  6. washeluting with methanol/chloroform (1:10)

Sources & evidence

ORD record
ord-7f02f5a71bbf4795be37180ed476c4a5
Source dataset
uspto-grants-2001_01
Patent number
US06169091A

Linked notes

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