Tetrahydrofuran → N-(4-methoxyphenyl)-2-phenylquinazolin-4-amine

HRID 2084071Notes

Reaction equation

HRID 2084071 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[N:3]=1.CO[C:20]1C=CC=[C:22]([NH2:26])[CH:21]=1.[H-].[Na+].[CH2:29]1[CH2:33][O:32][CH2:31][CH2:30]1>CCCCCC.CCOC(C)=O>[CH3:31][O:32][C:33]1[CH:29]=[CH:30][C:22]([NH:26][C:2]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[N:5]=[C:4]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[N:3]=2)=[CH:21][CH:20]=1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 108243-MethoxyanilineHCID 24758Sodium hydrideHCID 809774-Chloro-2-phenylquinazoline

Product 1

HCID 719284N-(4-methoxyphenyl)-2-phenylquinazolin-4-amineYield 22%

Reagents, catalysts & solvents 1

HCID 21226206Ethyl acetate hexaneSolvent

Procedure

To a solution of 4-chloro-2-phenylquinazoline (590 mg, 2.45 mmol) in THF (10 mL) was added m-anisidine (301 mg, 2.45 mmol) and NaH (60%, 120 mg, 3.0 mmol). The mixture was refluxed for 24 h. After cooled to room temperature, the mixture was diluted with 1:1 hexane/EtOAc (100 mL), washed with water and brine, dried over Na2SO4 and concentrated in vacuo. The residue was purified by chromatography (3:1 hexane/EtOAc) to yield the title compound as a white solid (173 mg, 0.53 mmol, 22%). 1H NMR (CDCl3): 8.54-8.51 (m, 2H), 8.00-7.74 (m, 5H), 7.52-7.47 (m, 4H), 7.38 (s, 1H), 7.02-7.00 (m, 2H), 3.88 (s, 3H).

Workup

  1. temperatureThe mixture was refluxed for 24 h
  2. washwashed with water and brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by chromatography (3:1 hexane/EtOAc)

Sources & evidence

ORD record
ord-2cc9fd1a2bcd401f804a5bb30348744a
Source dataset
uspto-grants-2004_04
Patent number
US06716851B2

Reaction notes

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