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

HRID 851909

Reaction equation

HRID 851909 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
150 °C

Procedure

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%).

Workup

  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

Sources & evidence

ORD record
ord-921ea4bdc99d4bf68bd35b95ceda85f6
Source dataset
uspto-grants-2007_08
Patent number
US07253166B2

Linked notes

Loading…