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

HRID 1787747Notes

Reaction equation

HRID 1787747 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-7bf8b5b452ce4684a8db2a4c4c018f0c
Source dataset
uspto-grants-2009_03
Patent number
US07511050B2

Reaction notes

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