Ethanol → Imatinib amine

HRID 2194968Notes

Reaction equation

HRID 2194968 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:14]=[C:13]([N+:15]([O-])=O)[CH:12]=[CH:11][C:10]=2[CH3:18])[N:5]=[C:4]([C:19]2[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=2)[CH:3]=1.O.C(O)C>[Pd].C(N(CC)CC)C>[CH3:18][C:10]1[CH:11]=[CH:12][C:13]([NH2:15])=[CH:14][C:9]=1[NH:8][C:6]1[N:5]=[C:4]([C:19]2[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=2)[CH:3]=[CH:2][N:7]=1

Participants

6

Reactant 3

HCID 702EthanolHCID 962WaterHCID 24897293HCID 24897293, compound

Product 1

HCID 9965429Imatinib amine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8471TriethylamineSolvent

Procedure

In an autoclave, 5 g 6-chloro-N-(2-methyl-5-nitrophenyl)-4-(3-pyridyl)-2-pyrimidine amine, 0.5 g palladium on charcoal 5% wet with 50% water, 50 mL ethanol and 5 mL triethylamine is charged. The mixture is hydrogenated at 5 bars and room temperature for 40 hours. Once completed the conversion, the catalyst is filtered off and the filtrates is concentrated in vacuum. The residue is taken again with isopropyl acetate and an aqueous carbonate solution. The layers are separated, and the organic layer is concentrated, yielding, upon drying, 3 g of product with 85% HPLC purity (A %), which is identified through LC-MS and 1H-NMR.

Workup

  1. filtrationthe catalyst is filtered off
  2. concentrationthe filtrates is concentrated in vacuum
  3. customThe layers are separated
  4. concentrationthe organic layer is concentrated
  5. customyielding
  6. customupon drying

Sources & evidence

ORD record
ord-8e90f50f809a4844aebba84e1b7b4505
Source dataset
uspto-grants-2012_12
Patent number
US08334381B2

Reaction notes

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