tert-Butyl 3-(2-amino-4-methyl-6-(pentylamino)pyrimidin-5-yl)prop-2-ynylcarbamate → tert-Butyl 3-(2-amino-4-methyl-6-(pentylamino)pyrimidin-5-yl)propylcarbamate

HRID 1617122Notes

Reaction equation

HRID 1617122 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([CH3:8])[C:5]([C:9]#[C:10][CH2:11][NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[C:4]([NH:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[N:3]=1>CCO.[Pd]>[NH2:1][C:2]1[N:7]=[C:6]([CH3:8])[C:5]([CH2:9][CH2:10][CH2:11][NH:12][C:13](=[O:19])[O:14][C:15]([CH3:16])([CH3:17])[CH3:18])=[C:4]([NH:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[N:3]=1

Participants

4

Reactant 1

HCID 86633393tert-Butyl 3-(2-amino-4-methyl-6-(pentylamino)pyrimidin-5-yl)prop-2-ynylcarbamate

Product 1

HCID 86633392tert-Butyl 3-(2-amino-4-methyl-6-(pentylamino)pyrimidin-5-yl)propylcarbamateYield 101.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

The product from step (iii) (3.7 g) was dissolved in EtOH (100 mL) then 5% Pd/C (300 mg) was added. The reaction mixture was hydrogenated at 3 bar for 16 h. The catalyst was removed by filtration and the solvent evaporated to give the subtitle compound 3.8 g.

Workup

  1. customThe catalyst was removed by filtration
  2. customthe solvent evaporated

Sources & evidence

ORD record
ord-3a1c5999ce704d44934c2f8842439c47
Source dataset
uspto-grants-2014_07
Patent number
US08765939B2

Reaction notes

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