2-(2-Hydroxyethyl)pyridine → HCID 21890798, compound

HRID 721430Notes

Reaction equation

HRID 721430 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][N:7]=[C:6]2[O:15][C:16]1[CH:22]=[CH:21][C:19]([NH2:20])=[C:18]([O:23][CH3:24])[CH:17]=1.Cl[C:26](Cl)([O:28][C:29](=[O:35])OC(Cl)(Cl)Cl)Cl.[N:37]1[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=1[CH2:43]CO.C(=O)(O)[O-].[Na+]>C(Cl)Cl.C(N(CC)CC)C.C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][N:7]=[C:6]2[O:15][C:16]1[CH:22]=[CH:21][C:19]([NH:20][C:29](=[O:35])[O:28][CH2:26][CH2:43][C:38]2[CH:39]=[CH:40][CH:41]=[CH:42][N:37]=2)=[C:18]([O:23][CH3:24])[CH:17]=1

Participants

8

Reactant 4

HCID 76752-(2-Hydroxyethyl)pyridineHCID 94429TriphosgeneHCID 516892Sodium BicarbonateHCID 218899914-[(6,7-Dimethoxy-4-quinazolinyl)oxy]-2-methoxyaniline

Product 1

HCID 21890798HCID 21890798, compoundYield 75.6%

Reagents, catalysts & solvents 3

HCID 1140TolueneSolventHCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

4-[(6,7-Dimethoxy-4-quinazolinyl)oxy]-2-methoxyaniline (100 mg) was added to toluene (10 ml) and triethylamine (1 ml), and the mixture was heated under reflux to prepare a solution. A solution of triphosgene (140 mg) in methylene chloride was then added thereto, and the mixture was heated under reflux for 10 min. Next, 2-(2-pyridyl)-1-ethanol (58 mg) was added thereto, and the mixture was further stirred with heating under reflux for 3 hr. A saturated aqueous sodium bicarbonate solution was added to stop the reaction, and the reaction solution was then extracted with chloroform, and the extract was washed with water and saturated brine in that order. The extract was dried over sodium sulfate and was then concentrated. The residue was purified on a column using chloroform/methanol to give the title compound (110 mg, yield 75%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux
  3. customto prepare a solution
  4. temperaturethe mixture was heated
  5. temperatureunder reflux for 10 min
  6. temperaturewith heating
  7. temperatureunder reflux for 3 hr
  8. customthe reaction
  9. extractionthe reaction solution was then extracted with chloroform
  10. washthe extract was washed with water and saturated brine in that order
  11. dry with materialThe extract was dried over sodium sulfate
  12. concentrationwas then concentrated
  13. customThe residue was purified on a column

Sources & evidence

ORD record
ord-ca10a64892c34b7094bed518b68d0d5d
Source dataset
uspto-grants-2006_11
Patent number
US07135466B2

Reaction notes

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