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 2046325Notes

Reaction equation

HRID 2046325 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-cd68196dba504c4195d9336f9a435ed8
Source dataset
uspto-grants-2013_11
Patent number
US08592435B2

Reaction notes

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