Ammonia methanol → 4-(8-Amino-7-methylquinazolin-4-ylamino)benzonitrile

HRID 1042258Notes

Reaction equation

HRID 1042258 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([N+:13]([O-])=O)[C:11]=1[CH3:12])[N:8]=[CH:7][N:6]=[C:5]2[NH:16][C:17]1[CH:24]=[CH:23][C:20]([C:21]#[N:22])=[CH:19][CH:18]=1.N.CO>CCO.[Pd]>[NH2:13][C:10]1[C:11]([CH3:12])=[CH:2][CH:3]=[C:4]2[C:9]=1[N:8]=[CH:7][N:6]=[C:5]2[NH:16][C:17]1[CH:24]=[CH:23][C:20]([C:21]#[N:22])=[CH:19][CH:18]=1

Participants

5

Reactant 2

HCID 21705897Ammonia methanolHCID 687269114-(6-Bromo-7-methyl-8-nitroquinazolin-4-ylamino)benzonitrile

Product 1

HCID 687253434-(8-Amino-7-methylquinazolin-4-ylamino)benzonitrileYield 83.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 4-(6-bromo-7-methyl-8-nitroquinazolin-4-ylamino)benzonitrile (400 mg, 1.04 mmol) and Pd/C (10%˜30 mg) in EtOH (20 mL) was stirred under H2 gas (1 atm) overnight. 30 mL of NH3/MeOH (2 M) was added and the mixture was filtered through celite and washed with MeOH/DCM (˜1:1). After removal of solvent the product was purified by flash chromatography eluting with MeOH/DCM (1-5%) to give 4-(8-amino-7-methylquinazolin-4-ylamino)benzonitrile (238 mg, 83%). MS (ESI, pos. ion) m/z: 276 [M+H]+

Workup

  1. filtrationthe mixture was filtered through celite
  2. washwashed with MeOH/DCM (˜1:1)
  3. customAfter removal of solvent the product
  4. customwas purified by flash chromatography
  5. washeluting with MeOH/DCM (1-5%)

Sources & evidence

ORD record
ord-ac3dab39775a42409fc7d0c0a41eccf2
Source dataset
uspto-grants-2013_10
Patent number
US08557830B2

Reaction notes

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