Acetic Acid → HCID 178424316, compound

HRID 430527Notes

Reaction equation

HRID 430527 reaction equation
C([N:8]1[C:16]2[C:15](=[O:17])[N:14]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[CH3:24])[C:13]([CH3:25])=[N:12][C:11]=2[NH:10][NH:9]1)C1C=CC=CC=1.C(O)(=O)C>[OH-].[OH-].[Pd+2].C(O)C>[CH3:25][C:13]1[N:14]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[CH3:24])[C:15](=[O:17])[C:16]2[N:8]=[N:9][NH:10][C:11]=2[N:12]=1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 18350685HCID 18350685, compound

Product 1

HCID 178424316HCID 178424316, compoundYield 17%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

A mixture of 1-benzyl-5-methyl-6-o-tolyl-3,6-dihydro-[1,2,3]triazolo[4,5-d]pyrimidin-7-one (4.0 g, 12.07 mmol), acetic acid (150 mL), ethanol (25 mL), and palladium hydroxide on carbon (4.0 g) was hydrogenated on a Parr apparatus. After 5 hours the catalyst was filtered off and replaced with fresh palladium hydroxide on carbon (4.0 g). The hydrogenation was continued 48 hours longer. The reaction was filtered and the filtrate was concentrated to afford 5-methyl-6-o-tolyl-3,6-dihydro-[1,2,3]triazolo[4,5-d]pyrimidin-7one (0.488 g, 17%) as a white powder.

Workup

  1. filtrationAfter 5 hours the catalyst was filtered off
  2. filtrationThe reaction was filtered
  3. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-8c8051506207424b8d0da09945c2f584
Source dataset
uspto-grants-2001_11
Patent number
US06323208B1

Reaction notes

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