Triethylamine → 8-methoxy-2-methylquinazoline

HRID 581783Notes

Reaction equation

HRID 581783 reaction equation
Cl[C:2]1[C:11]2[C:6](=[C:7]([O:12][CH3:13])[CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]([CH3:14])[N:3]=1.C(N(CC)CC)C>[Pd].C(OCC)(=O)C>[CH3:13][O:12][C:7]1[CH:8]=[CH:9][CH:10]=[C:11]2[C:6]=1[N:5]=[C:4]([CH3:14])[N:3]=[CH:2]2

Participants

5

Reactant 2

HCID 8471TriethylamineHCID 107747604-chloro-8-methoxy-2-methylquinazoline

Product 1

HCID 107735698-methoxy-2-methylquinazolineYield 71.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 4-chloro-8-methoxy-2-methylquinazoline (5.12 g), 10% palladium on carbon (512 mg) and triethylamine (3.72 g) in ethyl acetate (51 ml) was stirred under hydrogen atmosphere for 3 hours. The catalyst was removed by filtration, and the filtrate was concentrated. The residue was dissolved in methylene chloride, and the solution was washed with saturated sodium bicarbonate solution, water and brine, dried over magnesium sulfate, and concentrated. The residue was purified by silica gel column chromatography (methylene chloride-methanol) to give 8-methoxy-2-methylquinazoline (3.07 g). mp: 131-132° C.

Workup

  1. customThe catalyst was removed by filtration
  2. concentrationthe filtrate was concentrated
  3. dissolutionThe residue was dissolved in methylene chloride
  4. washthe solution was washed with saturated sodium bicarbonate solution, water and brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel column chromatography (methylene chloride-methanol)

Sources & evidence

ORD record
ord-937d557b8b954cc6b522c8b665e045a4
Source dataset
uspto-grants-1999_07
Patent number
US05922711

Reaction notes

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