Ethylene Glycol → 2-(7-bromo-2-chloro-5H-pyrimido[5,4-b]indol-4-yloxy)ethanol

HRID 1182846Notes

Reaction equation

HRID 1182846 reaction equation
[CH2:1]([OH:4])[CH2:2][OH:3].[H-].[Na+].[Br:7][C:8]1[CH:9]=[CH:10][C:11]2[C:12]3[N:20]=[C:19]([Cl:21])[N:18]=[C:17](Cl)[C:13]=3[NH:14][C:15]=2[CH:16]=1>C1COCC1>[Br:7][C:8]1[CH:9]=[CH:10][C:11]2[C:12]3[N:20]=[C:19]([Cl:21])[N:18]=[C:17]([O:3][CH2:2][CH2:1][OH:4])[C:13]=3[NH:14][C:15]=2[CH:16]=1

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 24758Sodium hydrideHCID 581184877-bromo-2,4-dichloro-5H-pyrimido[5,4-b]indole

Product 1

HCID 581185092-(7-bromo-2-chloro-5H-pyrimido[5,4-b]indol-4-yloxy)ethanolYield 88%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

397 mg (6.4 mmol) ethylene glycol was added to 115 mg (4.8 mmol) NaH in 20 ml THF and the mixture was stirred at room temperature for 30 min. Then, 500 mg (1.6 mmol) 7-bromo-2,4-dichloro-5H-pyrimido[5,4-b]indole (Example 4) was added and the mixture was refluxed for 5 h. Thereafter, the solvent was removed and the residue was taken up in acetic ester and washed with saturated NaCl solution, dried over Na2SO4 and filtrated. Having removed the solvent, 450 mg (88%) 2-(7-bromo-2-chloro-5H-pyrimido[5,4-b]indol-4-yloxy)ethanol was obtained. ESI-MS [m/z]: 342, 344 [M+H]+

Workup

  1. temperaturethe mixture was refluxed for 5 h
  2. customThereafter, the solvent was removed
  3. washwashed with saturated NaCl solution
  4. dry with materialdried over Na2SO4
  5. filtrationfiltrated
  6. customHaving removed the solvent

Sources & evidence

ORD record
ord-775bdc75bbf94a39a244d825c281b4e0
Source dataset
uspto-grants-2014_03
Patent number
US08664233B2

Reaction notes

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