Tert-butyl 2-(2-((1-benzylpiperidine-4-yl)(methyl)amino)-2-oxoethoxy)-4,6-dimethylpyrimidine-5-ylcarbamate → Tert-butyl 4,6-dimethyl-2-(2-(methyl(piperidine-4-yl)amino)-2-oxoethoxy)pyrimidine-5-ylcarbamate

HRID 2280898Notes

Reaction equation

HRID 2280898 reaction equation
C([N:8]1[CH2:13][CH2:12][CH:11]([N:14]([CH3:35])[C:15](=[O:34])[CH2:16][O:17][C:18]2[N:23]=[C:22]([CH3:24])[C:21]([NH:25][C:26](=[O:32])[O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[C:20]([CH3:33])[N:19]=2)[CH2:10][CH2:9]1)C1C=CC=CC=1>CO.[Pd]>[CH3:24][C:22]1[C:21]([NH:25][C:26](=[O:32])[O:27][C:28]([CH3:31])([CH3:29])[CH3:30])=[C:20]([CH3:33])[N:19]=[C:18]([O:17][CH2:16][C:15]([N:14]([CH3:35])[CH:11]2[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]2)=[O:34])[N:23]=1

Participants

4

Reactant 1

HCID 59336118Tert-butyl 2-(2-((1-benzylpiperidine-4-yl)(methyl)amino)-2-oxoethoxy)-4,6-dimethylpyrimidine-5-ylcarbamate

Product 1

HCID 59336171Tert-butyl 4,6-dimethyl-2-(2-(methyl(piperidine-4-yl)amino)-2-oxoethoxy)pyrimidine-5-ylcarbamateYield 96.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Pd—C (371 mg) was added to a solution of Compound 30 (3.7 g) in methanol (111 mL) and then, hydrogenation was carried out by stirring the mixture at atmospheric pressure and room temperature overnight. Subsequently, the catalyst was removed by filtration and the filtrate was concentrated under reduced pressure to give 2.9 g (96% yield) of the title compound.

Workup

  1. customSubsequently, the catalyst was removed by filtration
  2. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-9e0f5652587f4b188bc007ca302684c0
Source dataset
uspto-grants-2015_09
Patent number
US09139559B2

Reaction notes

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