2-(2-Methyl-5-nitroanilino)-4-(3-pyridyl)pyrimidine → Imatinib amine

HRID 736291Notes

Reaction equation

HRID 736291 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-])=O)=[CH:4][C:3]=1[NH:11][C:12]1[N:17]=[C:16]([C:18]2[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=2)[CH:15]=[CH:14][N:13]=1>C(OCC)(=O)C.C(O)C>[NH2:8][C:5]1[CH:6]=[CH:7][C:2]([CH3:1])=[C:3]([NH:11][C:12]2[N:17]=[C:16]([C:18]3[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=3)[CH:15]=[CH:14][N:13]=2)[CH:4]=1

Participants

4

Reactant 1

HCID 106861492-(2-Methyl-5-nitroanilino)-4-(3-pyridyl)pyrimidine

Product 1

HCID 9965429Imatinib amineYield 110.7%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

N-(2-methyl-5-nitrophenyl)-4-(3-pyridyl)-2-pyrimidine-amine (35 g, 0.114 mol) and stannous chloride dihydrate (128.5 g, 0.569 mol) were dissolved in a solvent mixture of ethyl acetate and ethanol (250 ml, 10/1, v/v), and the reaction solution was refluxed for 4 hours. The solution was cooled to room temperature, washed with 10% aqueous sodium hydroxide solution, and concentrated to give N-(5-amino-2-methylphenyl)-4-(3-pyridyl)-2-pyrimidine-amine (35 g).

Workup

  1. temperaturev/v), and the reaction solution was refluxed for 4 hours
  2. washwashed with 10% aqueous sodium hydroxide solution
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-9d490839a02c4b4eae2842b1aa2e95ed
Source dataset
uspto-grants-2009_09
Patent number
US07595323B2

Reaction notes

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