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

HRID 2368550Notes

Reaction equation

HRID 2368550 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].[CH:22](OCC)(OCC)OCC>>[CH2:1]([N:6]1[C:14]2[N:13]=[C:12]([C:15]([F:16])([F:18])[F:17])[NH:11][C:10]=2[C:9](=[O:19])[N:8]2[CH:22]=[N:21][N:20]=[C:7]12)[CH2:2][CH2:3][CH2:4][CH3:5]

Participants

3

Reactant 2

HCID 31214Ethyl orthoformateHCID 178446162HCID 178446162, compound

Product 1

HCID 250617109-pentyl-7-(trifluoromethyl)-6,9-dihydro-5H-[1,2,4]triazolo[4,3-a]purin-5-oneYield 227.3%

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 orthoformate (2 mL, 0.01 mol) 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 (0.1 g, 48%). LCMS calculated for C12H13F3N6O: (M+H) 315.1. Found: 315.1.

Workup

  1. concentrationThe reaction mixture was concentrated under vacuum
  2. customthe residue was purified by preparative LCMS
  3. customThe product fractions were collected

Sources & evidence

ORD record
ord-99cc6b2057104be6ad1ceb2a1a46523f
Source dataset
uspto-grants-2014_04
Patent number
US08703783B2

Reaction notes

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