Trifluoroacetic acid → 9-pentyl-3-(trifluoromethyl)-6,9-dihydro-5H-[1,2,4]triazolo[4,3-a]purin-5-one

HRID 2368591Notes

Reaction equation

HRID 2368591 reaction equation
[CH2:1]([N:6]1[C:14]2[N:13]=[CH:12][NH:11][C:10]=2[C:9](=[O:15])[NH:8]/[C:7]/1=[N:16]\[NH2:17])[CH2:2][CH2:3][CH2:4][CH3:5].[F:18][C:19]([F:24])([F:23])[C:20](O)=O>>[CH2:1]([N:6]1[C:14]2[N:13]=[CH:12][NH:11][C:10]=2[C:9](=[O:15])[N:8]2[C:20]([C:19]([F:24])([F:23])[F:18])=[N:17][N:16]=[C:7]12)[CH2:2][CH2:3][CH2:4][CH3:5]

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 178446164HCID 178446164, compound

Product 1

HCID 576003029-pentyl-3-(trifluoromethyl)-6,9-dihydro-5H-[1,2,4]triazolo[4,3-a]purin-5-oneYield 60.2%

Procedure

The mixture of (2E)-3-pentyl-3,7-dihydro-1H-purine-2,6-dione 2-hydrazone (200 mg, 0.85 mol) in trifluoroacetic acid (10 mL) was refluxed overnight. The reaction mixture was concentrated and purified by preparative LCMS to yield the desired product (160 mg, 60.2%). LCMS calculated for C12H14F3N6O (M+H): 315.1. Found 315.0.

Workup

  1. temperaturewas refluxed overnight
  2. concentrationThe reaction mixture was concentrated
  3. custompurified by preparative LCMS

Sources & evidence

ORD record
ord-d2c66ad111134096a752334011c9606a
Source dataset
uspto-grants-2014_04
Patent number
US08703783B2

Reaction notes

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