1-Benzyl-4-[N-ethyl-N-(6-chloro-5-nitro-4-pyrimidinyl)amino]piperidine → 1-Benzyl-4-[N-ethyl-N-(5-amino-4-pyrimidinyl)amino]piperidine

HRID 361865Notes

Reaction equation

HRID 361865 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([N:14]([CH2:25][CH3:26])[C:15]2[C:20]([N+:21]([O-])=O)=[C:19](Cl)[N:18]=[CH:17][N:16]=2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(O)C.[OH-].[Pd+2].[OH-]>[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([N:14]([CH2:25][CH3:26])[C:15]2[C:20]([NH2:21])=[CH:19][N:18]=[CH:17][N:16]=2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 544731551-Benzyl-4-[N-ethyl-N-(6-chloro-5-nitro-4-pyrimidinyl)amino]piperidine

Product 1

HCID 542746941-Benzyl-4-[N-ethyl-N-(5-amino-4-pyrimidinyl)amino]piperidine

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

1-Benzyl-4-[N-ethyl-N-(6-chloro-5-nitro-4-pyrimidinyl)amino]piperidine (EXAMPLE 252, 3.00 g) is dissolved in 150 ml of ethanol and 0.75 g of palladium hydroxide is added. The reaction is placed on a Parr hydrogenator at 10 psi for 1 h, then filtered through diatemous earth and concentrated under reduced pressure. Purification by flash column chromatography (5% methanol/chloroform) gives the title compound.

Workup

  1. filtrationfiltered through diatemous earth
  2. concentrationconcentrated under reduced pressure
  3. customPurification by flash column chromatography (5% methanol/chloroform)

Sources & evidence

ORD record
ord-3e186dcac467463c850100263db0234b
Source dataset
uspto-grants-1999_02
Patent number
US05866589

Reaction notes

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