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

HRID 564780

反応式

HRID 564780 の反応式
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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-7f02f5a71bbf4795be37180ed476c4a5
出典データセット
uspto-grants-2001_01
特許番号
US06169091A

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