Potassium Carbonate → {[4-[(3,4-Dichlorophenyl)amino]-6-(methyloxy)quinazolin-7-yl]oxy}acetonitrile

HRID 244565Notes

Reaction equation

HRID 244565 reaction equation
Br[CH2:2][C:3]#[N:4].[Cl:5][C:6]1[CH:7]=[C:8]([NH:13][C:14]2[C:23]3[C:18](=[CH:19][C:20]([OH:26])=[C:21]([O:24][CH3:25])[CH:22]=3)[N:17]=[CH:16][N:15]=2)[CH:9]=[CH:10][C:11]=1[Cl:12].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[Cl:5][C:6]1[CH:7]=[C:8]([NH:13][C:14]2[C:23]3[C:18](=[CH:19][C:20]([O:26][CH2:2][C:3]#[N:4])=[C:21]([O:24][CH3:25])[CH:22]=3)[N:17]=[CH:16][N:15]=2)[CH:9]=[CH:10][C:11]=1[Cl:12]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 11534BromoacetonitrileHCID 1362726214-(3,4-Dichloroanilino)-6-methoxyquinazolin-7(1H)-one

Product 1

HCID 66838691{[4-[(3,4-Dichlorophenyl)amino]-6-(methyloxy)quinazolin-7-yl]oxy}acetonitrileYield 91%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Bromoacetonitrile (2.1 ml, 30.1 mmol) was added to a mixture of 4-[(3,4-dichlorophenyl)amino]-6-(methyloxy)quinazolin-7-ol (10.12 g; 30.1 mmol) and potassium carbonate (16.6 g; 120.1 mmol) in DMF (200 ml). The mixture was stirred at room temperature overnight. The solvent was removed under high vacuum and the residue was triturated with water, filtered, washed with a mixture of hexane and ether (1/1) and dried under vacuum to give {[4-[(3,4-dichlorophenyl)amino]-6-(methyloxy)quinazolin-7-yl]oxy}acetonitrile (9.6 g; 91% yield). 1H NMR (400 MHz; DMSO-d6): 3.99 (s, 3H), 5.40 (s, 2H), 7.41 (s, 1H), 7.64 (d, 1H), 7.87 (dd, 1H), 7.90 (s, 1H), 8.23 (d, 1H), 8.57 (s, 1H), 9.69 (s, 1H); MS (EI) for C17H12Cl2N4O2: 375.06 (MH+).

Workup

  1. customThe solvent was removed under high vacuum
  2. customthe residue was triturated with water
  3. filtrationfiltered
  4. washwashed with a mixture of hexane and ether (1/1)
  5. customdried under vacuum

Sources & evidence

ORD record
ord-4f29d405ba6947fb9c46ed6fe300af46
Source dataset
uspto-grants-2014_02
Patent number
US08658654B2

Reaction notes

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