Ethylene Glycol → HCID 17965146, compound

HRID 1349948Notes

Reaction equation

HRID 1349948 reaction equation
[CH2:1]([OH:4])[CH2:2][OH:3].[H-].[Na+].F[C:8]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:9]=1[CH:10]=[N:11][C:12]([CH3:18])=[N:13]2>CN(C)C=O>[CH3:18][C:12]1[N:11]=[CH:10][C:9]2[C:14](=[CH:15][CH:16]=[CH:17][C:8]=2[O:3][CH2:2][CH2:1][OH:4])[N:13]=1

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 24758Sodium hydrideHCID 179651385-Fluoro-2-methylquinazoline

Product 1

HCID 17965146HCID 17965146, compoundYield 10%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of ethylene glycol (3.05 mL, 55.6 mmol) in N,N-dimethylformamide (50 mL) at room temperature was added sodium hydride (60% dispersion in oil, 0.30 g, 7.50 mmol) portion-wise. The reaction mixture was allowed to stir at room temperature for 30 minutes. A solution of 5-fluoro-2-methylquinazoline (2.22 g, 55.6 mmol) in N,N-dimethylformamide (5 mL) was added and the reaction mixture heated at 85° C. for 14 h. The mixture was allowed to cool to room temperature, quenched by the addition of water and concentrated in vacuo. Chromatography of the residue on SiO2 eluting with 40% ethyl acetate in dichloromethane to ethyl acetate gave the title compound as a yellow solid (0.39 g, 10%).

Workup

  1. temperaturethe reaction mixture heated at 85° C. for 14 h
  2. temperatureto cool to room temperature
  3. customquenched by the addition of water
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-fbe1214714954be799f1cb732d4ee832
Source dataset
uspto-grants-2007_05
Patent number
US07214674B2

Reaction notes

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