Diisopropylethylamine → 5,8-Dimethyl-[1,2,4]triazolo[1,5-a]pyrazin-2-ylamine

HRID 1054980Notes

Reaction equation

HRID 1054980 reaction equation
Cl.NO.C([N:7](CC)C(C)C)(C)C.C(OC(=O)[NH:17][C:18](=S)[NH:19][C:20]1[C:25]([CH3:26])=[N:24][CH:23]=[C:22]([CH3:27])[N:21]=1)C>C(O)C.O>[CH3:27][C:22]1[N:21]2[N:7]=[C:18]([NH2:17])[N:19]=[C:20]2[C:25]([CH3:26])=[N:24][CH:23]=1

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 443297Hydroxyamine hydrochlorideHCID 90017035ethyl-N-[(3,6-dimethylpyrazin-2-yl)carbamothioyl]carbamate

Product 1

HCID 900260875,8-Dimethyl-[1,2,4]triazolo[1,5-a]pyrazin-2-ylamineYield 71.87%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
25 °C

Procedure

A mixture of hydroxylamine hydrochloride (13.68 g, 196.85 mmol) and N,N-diisopropylethylamine (20.6 ml, 118.11 mmol) in ethanol (200 ml) was stirred for 10 minutes at 25° C. To this mixture was then added ethyl-N-[(3,6-dimethylpyrazin-2-yl)carbamothioyl]carbamate (10 g, 39.37 mmol), and the resultant mixture was heated under reflux for 16 hours. The resultant mixture was diluted with water (100 ml), stirred for 10 min, and extracted twice with ethyl acetate. The combined organic layers were washed with brine, dried over anhydrous sodium sulfate, filtered and evaporated. The crude material thus obtained was triturated with hexane affording 5,8-dimethyl-[1,2,4]triazolo[1,5-a]pyrazin-2-ylamine (2.4 g, 71.87%) as a white solid. MS: m/z=164 (M+H+)

Workup

  1. temperatureunder reflux for 16 hours
  2. stirringstirred for 10 min
  3. extractionextracted twice with ethyl acetate
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. customThe crude material thus obtained
  9. customwas triturated with hexane

Sources & evidence

ORD record
ord-8de2091aaabf40168ebedbcd007daf41
Source dataset
uspto-grants-2016_07
Patent number
US09394311B2

Reaction notes

Loading…