Benzyl 4-(2-amino-4-methyl-6-(pentylamino)pyrimidin-5-yl)but-3-ynylcarbamate → 5-(4-Aminobutyl)-6-methyl-N4-pentylpyrimidine-2,4-diamine

HRID 1617133Notes

Reaction equation

HRID 1617133 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([CH3:8])[C:5]([C:9]#[C:10][CH2:11][CH2:12][NH:13]C(=O)OCC2C=CC=CC=2)=[C:4]([NH:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])[N:3]=1>CCO.[Pd]>[NH2:13][CH2:12][CH2:11][CH2:10][CH2:9][C:5]1[C:4]([NH:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])=[N:3][C:2]([NH2:1])=[N:7][C:6]=1[CH3:8]

Participants

4

Reactant 1

HCID 68957321Benzyl 4-(2-amino-4-methyl-6-(pentylamino)pyrimidin-5-yl)but-3-ynylcarbamate

Product 1

HCID 684176515-(4-Aminobutyl)-6-methyl-N4-pentylpyrimidine-2,4-diamineYield 44.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent2×

Procedure

The product from step (i) (0.2 g) was dissolved in EtOH (20 mL) then 5% Pd/C (100 mg) in EtOH (5 mL) was added. The reaction mixture was hydrogenated at 4 bar overnight. The catalyst was filtered off then 20% Pd(OH)2/C (100 mg) in EtOH (5 ml) was added and the reaction mixture hydrogenated at 4 bar for 3 h. The catalyst was filtered off and the solvents evaporated to give the subtitle compound 0.06 g.

Workup

  1. customwas hydrogenated at 4 bar overnight
  2. filtrationThe catalyst was filtered off
  3. addition20% Pd(OH)2/C (100 mg) in EtOH (5 ml) was added
  4. filtrationThe catalyst was filtered off
  5. customthe solvents evaporated

Sources & evidence

ORD record
ord-465ad4720dff4a809faa7dc2c09aef41
Source dataset
uspto-grants-2014_07
Patent number
US08765939B2

Reaction notes

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