3-Bromoaniline → N-(3-bromophenyl)pyrido[3,4-d]pyrimidin-4-amine

HRID 1386195노트

반응식

HRID 1386195 반응식
CS[C:3]1[C:4]2[CH:12]=[CH:11][N:10]=[CH:9][C:5]=2[N:6]=[CH:7][N:8]=1.[Br:13][C:14]1[CH:15]=[C:16]([CH:18]=[CH:19][CH:20]=1)[NH2:17]>>[Br:13][C:14]1[CH:15]=[C:16]([CH:18]=[CH:19][CH:20]=1)[NH:17][C:3]1[C:4]2[CH:12]=[CH:11][N:10]=[CH:9][C:5]=2[N:6]=[CH:7][N:8]=1

참가 물질

3

반응물 2

HCID 115623-BromoanilineHCID 232404654-Methylthiopyrido[3,4-d]pyrimidine

생성물 1

HCID 5328257N-(3-bromophenyl)pyrido[3,4-d]pyrimidin-4-amine수율 52.7%

반응 조건

온도
100 °C

실험 절차

A mixture of 4-methylthiopyrido[3,4-d]pyrimidine (75 mg, 0.42 mmol) (see previous experimental), and 3-bromoaniline (1 mL) is heated to 100° C. under N2 for 2 h. The reaction mixture is then chromatographed on silica using MPLC and eluting with a gradient system (CHCl3 to 5% MeOH in CHCl3) The fractions are concentrated under reduced pressure, and the resulting solid is recrystallized from Et2O to yield 4-(3-bromoanilino)pyrido[3,4-d]pyrimidine (66 mg, 52.7%) as a light brown solid. 1H NMR (DMSO) δ 10.15 (1H, s), 9.21 (1H, s), 8.80 (1H, s), 8.76 (1H, d, J=5.8 Hz), 8.44 (1H, d, J=5.6 Hz), 8.25 (1H, s), 7.93 (1H, d, J=7.7 Hz), 7.45-7.37 (2H, m).

후처리

  1. customThe reaction mixture is then chromatographed on silica using MPLC
  2. washeluting with a gradient system (CHCl3 to 5% MeOH in CHCl3) The fractions
  3. concentrationare concentrated under reduced pressure
  4. customthe resulting solid is recrystallized from Et2O

출처 및 근거

ORD 기록
ord-01fd1b770cba41cd910c154750a18b0d
출처 데이터셋
uspto-grants-2001_07
특허 번호
US06265410B1

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