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

HRID 564780

반응식

HRID 564780 반응식
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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-7f02f5a71bbf4795be37180ed476c4a5
출처 데이터셋
uspto-grants-2001_01
특허 번호
US06169091A

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