tert-Butyl [1,2,4]triazolo[1,5-a]pyrazin-2-ylcarbamate → tert-Butyl (5,6,7,8-tetrahydro-[1,2,4]triazolo[1,5-a]pyrazin-2-yl)carbamate

HRID 1022105Notes

Reaction equation

HRID 1022105 reaction equation
[C:1]([O:5][C:6](=[O:17])[NH:7][C:8]1[N:16]=[C:11]2[CH:12]=[N:13][CH:14]=[CH:15][N:10]2[N:9]=1)([CH3:4])([CH3:3])[CH3:2]>[Pd].C(O)C>[N:16]1[C:8]([NH:7][C:6](=[O:17])[O:5][C:1]([CH3:3])([CH3:2])[CH3:4])=[N:9][N:10]2[CH2:15][CH2:14][NH:13][CH2:12][C:11]=12

Participants

4

Reactant 1

HCID 89548973tert-Butyl [1,2,4]triazolo[1,5-a]pyrazin-2-ylcarbamate

Product 1

HCID 86684511tert-Butyl (5,6,7,8-tetrahydro-[1,2,4]triazolo[1,5-a]pyrazin-2-yl)carbamateYield 68.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

A 100-mL round-bottomed flask was purged with nitrogen and charged with 270c (1.0 g, 4.25 mmol), 20% palladium on carbon (10% wet, 200 mg), and ethanol (40 mL). It was then evacuated, charged with hydrogen gas (25 atm), and stirred at 60° C. for 24 h. The hydrogen was evacuated and nitrogen was charged into the flask. The catalyst was removed by filtration through a pad of CELITE® and the filtrate was concentrated under reduced pressure to afford 270d (700 mg, 68%). MS-ESI: [M-t-Bu]+ 184.0

Workup

  1. customA 100-mL round-bottomed flask was purged with nitrogen
  2. customIt was then evacuated
  3. additioncharged with hydrogen gas (25 atm)
  4. customThe hydrogen was evacuated
  5. additionnitrogen was charged into the flask
  6. customThe catalyst was removed by filtration through a pad of CELITE®
  7. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-a3f2a6cd4b034b178ac34925170baac2
Source dataset
uspto-grants-2014_05
Patent number
US08716274B2

Reaction notes

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