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

HRID 564780

Reaktionsgleichung

Reaktionsgleichung von HRID 564780
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

Komponenten

4

Edukt 2

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

Produkt 1

HCID 221128934-(4-Benzyloxyanilino)pyrido[2,3-d]pyrimidineAusbeute 6,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-7f02f5a71bbf4795be37180ed476c4a5
Quelldatensatz
uspto-grants-2001_01
Patentnummer
US06169091A

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