6-(2,6-Dichloro-3,5-dimethoxyphenyl)-N-(2-methyl-6-nitrophenyl)-2-quinazolinamine → HCID 86713565, compound

HRID 2274181Notes

Reaction equation

HRID 2274181 reaction equation
[Cl:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][C:5]([O:10][CH3:11])=[C:4]([Cl:12])[C:3]=1[C:13]1[CH:14]=[C:15]2[C:20](=[CH:21][CH:22]=1)[N:19]=[C:18]([NH:23][C:24]1[C:29]([N+:30]([O-])=O)=[CH:28][CH:27]=[CH:26][C:25]=1[CH3:33])[N:17]=[CH:16]2>CO.C(OCC)(=O)C.[Pd]>[Cl:12][C:4]1[C:5]([O:10][CH3:11])=[CH:6][C:7]([O:8][CH3:9])=[C:2]([Cl:1])[C:3]=1[C:13]1[CH:14]=[C:15]2[C:20](=[CH:21][CH:22]=1)[N:19]=[C:18]([NH:23][C:24]1[C:29]([NH2:30])=[CH:28][CH:27]=[CH:26][C:25]=1[CH3:33])[N:17]=[CH:16]2

Participants

5

Reactant 1

HCID 867135666-(2,6-Dichloro-3,5-dimethoxyphenyl)-N-(2-methyl-6-nitrophenyl)-2-quinazolinamine

Product 1

HCID 86713565HCID 86713565, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

6-(2,6-dichloro-3,5-dimethoxyphenyl)-N-(2-methyl-6-nitrophenyl)quinazolin-2-amine (5.5 g, 11.33 mmol) was taken up in methanol (200 ml) and Ethyl Acetate (100 ml), 10% Pd/C (650 mg) was added. The mixture was stirred under H2 balloon overnight. The reaction mixture was filtered through celite and the solvent was removed to give N1-(6-(2,6-dichloro-3,5-dimethoxyphenyl)quinazolin-2-yl)-6-methylbenzene-1,2-diamine in quantitative yield. It was carried on to the next step without further purification. MS (ES+) C23H20Cl2N4O2, 455 [M+H]+

Workup

  1. filtrationThe reaction mixture was filtered through celite
  2. customthe solvent was removed

Sources & evidence

ORD record
ord-90fc2f2c7f3a44288a9679c627fa977c
Source dataset
uspto-grants-2015_09
Patent number
US09126951B2

Reaction notes

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