Acetic Acid → HCID 178424316, compound

HRID 1737272Notes

Reaction equation

HRID 1737272 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-7-one (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-56d6403057fd494faa3c4a41e025309b
Source dataset
uspto-grants-1999_10
Patent number
US05962457

Reaction notes

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