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

HRID 2368549Notes

Reaction equation

HRID 2368549 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-9e22a77879144938b6e7299dc1acd750
Source dataset
uspto-grants-2014_04
Patent number
US08703783B2

Reaction notes

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