Resorcinol → 3-[(6-bromo-7H-pyrrolo[2,3-d]pyrimidin-4-yl)oxy]phenol

HRID 851909

반응식

HRID 851909 반응식
[Br:1][C:2]1[NH:11][C:5]2[N:6]=[CH:7][N:8]=[C:9](Cl)[C:4]=2[CH:3]=1.[C:12]1([CH:19]=[CH:18][CH:17]=[C:15]([OH:16])[CH:14]=1)[OH:13].C(N(C(C)C)CC)(C)C>O1CCOCC1>[Br:1][C:2]1[NH:11][C:5]2[N:6]=[CH:7][N:8]=[C:9]([O:13][C:12]3[CH:19]=[CH:18][CH:17]=[C:15]([OH:16])[CH:14]=3)[C:4]=2[CH:3]=1

참가 물질

5

반응물 3

HCID 5054ResorcinolHCID 81531DiisopropylethylamineHCID 457898276-Bromo-4-chloro-7H-pyrrolo[2,3-D]pyrimidine

생성물 1

HCID 694901713-[(6-bromo-7H-pyrrolo[2,3-d]pyrimidin-4-yl)oxy]phenol수율 32.7%

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

반응 조건

온도
150 °C

실험 절차

6-Bromo-4-chloro-7H-pyrrolo[2,3-d]pyrimidine (100 mg, 0.41 mmol), prepared as in reference 1, is mixed with resorcinol (451 mg, 4.1 mmol) and diisopropylethylamine (714 μL, 4.1 mmol) in dioxane (1.3 mL). The mixture is heated to 150° C. for 3 days, with stirring. The reaction is then cooled to ambient temperature and the solvent is removed. The resultant crude product is purified by flash column chromatography using a gradient of 3-5% MeOH in DCM to yield 5-(6-bromo-7H-pyrrolo[2,3-d]pyrimidin-4-yloxyl)-phenol (41 mg; 32%).

후처리

  1. temperatureThe reaction is then cooled to ambient temperature
  2. customthe solvent is removed
  3. customThe resultant crude product is purified by flash column chromatography

출처 및 근거

ORD 기록
ord-921ea4bdc99d4bf68bd35b95ceda85f6
출처 데이터셋
uspto-grants-2007_08
특허 번호
US07253166B2

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