Sodium Hydroxide → 8-Iodo-[1,2,4]triazolo[1,5-a]pyrazin-2-amine

HRID 2272996Notes

Reaction equation

HRID 2272996 reaction equation
Cl[C:2]1[C:3]2[N:4]([N:8]=[C:9]([NH2:11])[N:10]=2)[CH:5]=[CH:6][N:7]=1.[IH:12].[OH-].[Na+]>O>[I:12][C:2]1[C:3]2[N:4]([N:8]=[C:9]([NH2:11])[N:10]=2)[CH:5]=[CH:6][N:7]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 24841Hydrogen iodideHCID 772310108-Chloro-[1,2,4]triazolo[1,5-a]pyrazin-2-amine

Product 1

HCID 772308038-Iodo-[1,2,4]triazolo[1,5-a]pyrazin-2-amineYield 92.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
50 °C

Procedure

8-Chloro-[1,2,4]triazolo[1,5-a]pyrazin-2-ylamine (5.500 g; 32.43 mmol) is suspended in water (40.0 ml) before HI (67%, 21.855 ml; 194 mmol) is added. The mixture is stirred at 50° C. for 16 h and monitored by HPLC. The mixture is cooled to Rt, diluted with water. After adding NaOH till pH 14 is reached, the resulting suspension is cooled to 0° C. and all solids are filtered off giving 8-Iodo-[1,2,4]triazolo[1,5-a]pyrazin-2-ylamine (7.850 g; 30.074 mmol) as a yellow solid.

Workup

  1. additionis added
  2. temperatureThe mixture is cooled to Rt
  3. temperaturethe resulting suspension is cooled to 0° C.
  4. filtrationall solids are filtered off

Sources & evidence

ORD record
ord-1afaa960e94f4ed98931487ce74d5e7c
Source dataset
uspto-grants-2015_09
Patent number
US09120804B2

Reaction notes

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