Hydrochloric Acid → 6-Pentyl-6,9-dihydro-5H-[1,2,4]triazolo[3,4-i]purin-5-one

HRID 600576Notes

Reaction equation

HRID 600576 reaction equation
C([N:8]1[C:16]2[C:15]3=[N:17][N:18]=[CH:19][N:14]3[C:13](=[O:20])[N:12]([CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[C:11]=2[N:10]=[CH:9]1)C1C=CC=CC=1.Cl>C(O)(=O)C.[OH-].[Pd+2].[OH-]>[CH2:21]([N:12]1[C:11]2[N:10]=[CH:9][NH:8][C:16]=2[C:15]2=[N:17][N:18]=[CH:19][N:14]2[C:13]1=[O:20])[CH2:22][CH2:23][CH2:24][CH3:25]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 598538329-Benzyl-6-pentyl-6,9-dihydro-5H-[1,2,4]triazolo[3,4-i]purin-5-one

Product 1

HCID 1359846986-Pentyl-6,9-dihydro-5H-[1,2,4]triazolo[3,4-i]purin-5-oneYield 65.8%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalyst2×HCID 176Acetic AcidSolvent

Procedure

To a mixture of 9-benzyl-6-pentyl-6,9-dihydro-5H-[1,2,4]triazolo[3,4-i]purin-5-one (0.25 g, 0.74 mmol) in acetic acid (20 mL) was added palladium hydroxide (0.20 g, 1.4 mmol) under N2. The mixture was shaken under H2 at 60 psi overnight. Since the reaction was not complete, more palladium hydroxide (0.2 g, 1.4 mmol) and concentrated HCl (1 mL) were added. The resulting mixture was shaken under H2 at 60 psi overnight. The reaction solution was filtered and the filtrate was concentrated under vacuum to provide the product as a white solid (0.12 g, 65.6%). LCMS calculated for C11H15N6O (M+H): 247.1. found: 247.1.

Workup

  1. stirringThe resulting mixture was shaken under H2 at 60 psi overnight
  2. filtrationThe reaction solution was filtered
  3. concentrationthe filtrate was concentrated under vacuum

Sources & evidence

ORD record
ord-ebb3db9058bc41bc8abd59e69d6ab06f
Source dataset
uspto-grants-2011_03
Patent number
US07902205B2

Reaction notes

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