Sodium ethoxide → 6-Bromo-4-ethoxyquinazoline

HRID 1783624Notes

Reaction equation

HRID 1783624 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][N:6]=[C:5]2Cl.[O-:13][CH2:14][CH3:15].[Na+]>C(O)C>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][N:6]=[C:5]2[O:13][CH2:14][CH3:15]

Participants

4

Reactant 2

HCID 2723922Sodium ethoxideHCID 167703106-Bromo-4-chloro-quinazoline

Product 1

HCID 7307686-Bromo-4-ethoxyquinazolineYield 55%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The suspension of 6-bromo-4-chloro-quinazoline (4.87 g, 20 mmol), sodium ethoxide (95%, 14.32 g, 200 mmol) in anhydrous ethyl alcohol (150 ml) was stirred at room temperature for 4 hr. After the reaction, solvent was evaporated. Then, ice water was added, followed by addition of 3 N HCL aq to adjust the pH to 9, and precipitate formed. The solid was collected and washed with H2O three times, then dried. Flash chromatography (Merck silica gel 60, 230-400 mesh, 10%-50% ethyl acetate in hexane for 30 min) afforded 6-Bromo-4-ethoxy-quinazoline (2.13 g, 55%) as a light yellow solid. LC-MS m/e 254 (MH+).

Workup

  1. customAfter the reaction, solvent
  2. customwas evaporated
  3. additionThen, ice water was added
  4. additionfollowed by addition of 3 N HCL aq
  5. customformed
  6. customThe solid was collected
  7. washwashed with H2O three times
  8. customdried

Sources & evidence

ORD record
ord-95da9d0afaa44711bde8cfef46cdfe2c
Source dataset
uspto-grants-2009_03
Patent number
US07501428B2

Reaction notes

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