5-bromo-7-methyl-8-nitro-N-(3-(trifluoromethyl)phenyl)quinazolin-4-amine → 7-methyl-N4-(3-(trifluoromethyl)phenyl)quinazoline-4,8-diamine

HRID 1469762Notes

Reaction equation

HRID 1469762 reaction equation
Br[C:2]1[CH:11]=[C:10]([CH3:12])[C:9]([N+:13]([O-])=O)=[C:8]2[C:3]=1[C:4]([NH:16][C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([C:23]([F:26])([F:25])[F:24])[CH:18]=1)=[N:5][CH:6]=[N:7]2>CCO.[Pd]>[CH3:12][C:10]1[C:9]([NH2:13])=[C:8]2[C:3]([C:4]([NH:16][C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([C:23]([F:26])([F:24])[F:25])[CH:18]=3)=[N:5][CH:6]=[N:7]2)=[CH:2][CH:11]=1

Participants

4

Reactant 1

HCID 866922515-bromo-7-methyl-8-nitro-N-(3-(trifluoromethyl)phenyl)quinazolin-4-amine

Product 1

HCID 673386327-methyl-N4-(3-(trifluoromethyl)phenyl)quinazoline-4,8-diamineYield 66.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of 5-bromo-7-methyl-8-nitro-N-(3-(trifluoromethyl)phenyl)quinazolin-4-amine (400 mg, 0.94 mmol) in EtOH (10 mL) was added 10% Pd/C (420 mg) and the suspension was stirred under H2 (1 atm) for 5 h. Then the reaction mixture was filtered through celite and concentrated. The residue was purified by column chromatography to afford 200 mg of the title product. 1H NMR (300 MHz, DMSO-d6): δ 9.73 (s, 1H), 8.59 (s, 1H), 8.38 (s, 1H), 8.26 (d, J=7.2 Hz, 1H), 7.65-7.58 (m, 2H), 7.42 (d, J=7.2 Hz, 1H), 7.30 (d, J=8.7 Hz, 1H), 5.63 (br s, 2H), 2.80 (s, 3H).

Workup

  1. filtrationThen the reaction mixture was filtered through celite
  2. concentrationconcentrated
  3. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-bb3c9e7f22b8409b8816c00c5a3691f1
Source dataset
uspto-grants-2015_04
Patent number
US09006257B2

Reaction notes

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