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

HRID 1766990Notes

Reaction equation

HRID 1766990 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.[Pd]>[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 amine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A suspension of N-(2-methyl-5-nitrophenyl)-4-(3-pyridyl)-2-pyrimidine-amine (1.5 g, 4.6 mmol) and palladium on active carbon (150 mg, 10%) in ethyl acetate (100 ml) was hydrogenated under a hydrogen atmosphere for 2 hours. The reaction was filtered and the filtrate was concentrated to give N-(5-amino-2-methylphenyl)-4-(3-pyridyl)-2-pyrimidine-amine for future use without further purification.

Workup

  1. filtrationThe reaction was filtered
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-a31234fddb154a41be7a5bb5aaabab32
Source dataset
uspto-grants-2007_06
Patent number
US07232825B2

Reaction notes

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