Triethyl orthoacetate → 3-Methyl-9-pentyl-7-(trifluoromethyl)-6,9-dihydro-5H-[1,2,4]triazolo[4,3-a]purin-5-one

HRID 1787746Notes

Reaction equation

HRID 1787746 reaction equation
[CH2:1]([N:6]1[C:14]2[N:13]=[C:12]([C:15]([F:18])([F:17])[F:16])[NH:11][C:10]=2[C:9](=[O:19])[NH:8]/[C:7]/1=[N:20]\[NH2:21])[CH2:2][CH2:3][CH2:4][CH3:5].[C:22](OCC)(OCC)(OCC)[CH3:23]>>[CH3:22][C:23]1[N:8]2[C:9](=[O:19])[C:10]3[NH:11][C:12]([C:15]([F:16])([F:18])[F:17])=[N:13][C:14]=3[N:6]([CH2:1][CH2:2][CH2:3][CH2:4][CH3:5])[C:7]2=[N:20][N:21]=1

Participants

3

Reactant 2

HCID 66221Triethyl orthoacetateHCID 178446162HCID 178446162, compound

Product 1

HCID 441882883-Methyl-9-pentyl-7-(trifluoromethyl)-6,9-dihydro-5H-[1,2,4]triazolo[4,3-a]purin-5-one

Procedure

A mixture of (2E)-3-pentyl-8-(trifluoromethyl)-3,7-dihydro-1H-purine-2,6-dione-2-hydrazone (0.020 g, 0.14 mmol) and triethyl orthoacetate (2 mL, 10 mmol) was stirred at room temperature for 1 h. The reaction mixture was concentrated under vacuum and the residue was purified by preparative LCMS. The product fractions were collected and lyophilized to yield pure product as white powder. LCMS calculated for C13H15F3N6O: (M+H) 329.1; found: 329.1.

Workup

  1. concentrationThe reaction mixture was concentrated under vacuum
  2. customthe residue was purified by preparative LCMS
  3. customThe product fractions were collected
  4. customto yield pure product as white powder

Sources & evidence

ORD record
ord-7460d3dbb3654fe8ac42ae7a7e072513
Source dataset
uspto-grants-2009_03
Patent number
US07511050B2

Reaction notes

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