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 2387774Notes

Reaction equation

HRID 2387774 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-a641c781d67e4806b6004b0c515ea5e8
Source dataset
uspto-grants-2012_09
Patent number
US08268990B2

Reaction notes

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