Ammonia → [1,2,4]Triazolo[1,5-a]pyrazin-8-amine, 6-bromo-2-(2-furanyl)-

HRID 2242888Notes

Reaction equation

HRID 2242888 reaction equation
[NH3:1].[Br:2][C:3]1[N:4]=[C:5](Br)[C:6]2[N:7]([N:9]=[C:10]([C:12]3[O:13][CH:14]=[CH:15][CH:16]=3)[N:11]=2)[CH:8]=1>O1CCOCC1>[Br:2][C:3]1[N:4]=[C:5]([NH2:1])[C:6]2[N:7]([N:9]=[C:10]([C:12]3[O:13][CH:14]=[CH:15][CH:16]=3)[N:11]=2)[CH:8]=1

Participants

4

Reactant 2

HCID 222Ammonia2×HCID 860075466,8-Dibromo-2-furan-2-yl-[1,2,4]triazolo[1,5-a]pyrazine

Product 1

HCID 71401630[1,2,4]Triazolo[1,5-a]pyrazin-8-amine, 6-bromo-2-(2-furanyl)-Yield 99%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Anhydrous ammonia was bubbled over a one-hour period into a solution of 6,8-dibromo-2-furan-2-yl-[1,2,4]triazolo[1,5-a]pyrazine (18.4 g, 0.054 mol) in dioxane (400 ml). The resulting mixture was stirred at room temperature for 2 days during which time the solution was twice recharged with ammonia by bubbling in for one hour. After concentration, diethyl ether (200 ml) was added and the resulted yellow slurry was stirred at room temperature for overnight. 6-Bromo-2-furan-2-yl-[1,2,4]triazolo[1,5-a]pyrazin-8-ylamine was then collected and- dried (15 g, 99% yield). 1H NMR (300 MHz, CDCl3) δ 6.70 (dd, 1H), 7.10 (d, 1H), 7.8-8.0 (br m, 3H), 8.58 (s, 1H). MS: m/z: 280 [M+H]+.

Workup

  1. customby bubbling in for one hour
  2. concentrationAfter concentration, diethyl ether (200 ml)
  3. additionwas added
  4. stirringthe resulted yellow slurry was stirred at room temperature for overnight
  5. custom6-Bromo-2-furan-2-yl-[1,2,4]triazolo[1,5-a]pyrazin-8-ylamine was then collected
  6. custom- dried (15 g, 99% yield)

Sources & evidence

ORD record
ord-0bd5066612f2480ba26839c01254ea6c
Source dataset
uspto-grants-2010_03
Patent number
US07674791B2

Reaction notes

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