Hydrogen iodide → 2-Furan-2-yl-6-iodo-[1,2,4]triazolo[1,5-a]pyrazin-8-ylamine

HRID 2242900Notes

Reaction equation

HRID 2242900 reaction equation
Br[C:2]1[N:3]=[C:4]([NH2:16])[C:5]2[N:6]([N:8]=[C:9]([C:11]3[O:12][CH:13]=[CH:14][CH:15]=3)[N:10]=2)[CH:7]=1.[IH:17]>CCO>[O:12]1[CH:13]=[CH:14][CH:15]=[C:11]1[C:9]1[N:10]=[C:5]2[C:4]([NH2:16])=[N:3][C:2]([I:17])=[CH:7][N:6]2[N:8]=1

Participants

4

Reactant 2

HCID 24841Hydrogen iodideHCID 71401630[1,2,4]Triazolo[1,5-a]pyrazin-8-amine, 6-bromo-2-(2-furanyl)-

Product 1

HCID 866099442-Furan-2-yl-6-iodo-[1,2,4]triazolo[1,5-a]pyrazin-8-ylamineYield 92%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 6-bromo-2-furan-2-yl-[1,2,4]triazolo[1,5-a]pyrazin-8-ylamine (600 mg; see Examples 1 and 2 above) and 57% HI (10 mL) in EtOH (50 mL) was refluxed for 1 hour. The solvent was removed in vacuo and the residue was triturated with H2O to afford 2-furan-2-yl-6-iodo-[1,2,4]triazolo[1,5-a]pyrazin-8-ylamine as a brown solid (642 mg, 92%). 1H NMR (300 MHz, DMSO-d6) δ 6.8 (dd, J3.4, 1.8 Hz, 1H), 7.2 (dd, J=3.4, 0.8 Hz, 1H), 7.95 (s, 1H), 8.6 (s, 1H). MS: m/z 327 [M+H]+.

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue was triturated with H2O

Sources & evidence

ORD record
ord-33cf3c84a67f4b0e8d84e23febc66460
Source dataset
uspto-grants-2010_03
Patent number
US07674791B2

Reaction notes

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