2-Bromopropane → HCID 90273228, compound

HRID 1053112Notes

Reaction equation

HRID 1053112 reaction equation
[CH:1](Br)([CH3:3])[CH3:2].[N-:5]=[N+:6]=[N-:7].[Na+].[Br:9][C:10]1[N:11]=[C:12]([C:17]#[CH:18])[C:13]([NH2:16])=[N:14][CH:15]=1>CC(O)(C)C.O.CCOC(C)=O.[Cu]I>[Br:9][C:10]1[N:11]=[C:12]([C:17]2[N:5]=[N:6][N:7]([CH:1]([CH3:3])[CH3:2])[CH:18]=2)[C:13]([NH2:16])=[N:14][CH:15]=1

Participants

7

Reactant 3

HCID 63582-BromopropaneHCID 33557Sodium AzideHCID 457896185-Bromo-3-ethynylpyrazin-2-amine

Product 1

HCID 90273228HCID 90273228, compound

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 8857Ethyl AcetateSolventHCID 714019492-Methylpropan-2-ol--water (1/1)Solvent

Conditions

Temperature
80 °C

Procedure

A mixture of isopropyl bromide (2.5 g, 20.3 mmol) and sodium azide (1.3 g, 20.3 mmol) in t-BuOH/water (1:2) (25 mL) was stirred for 2 h at 80° C. Then the reaction mixture was cooled to room temperature, was added 5-bromo-3-ethynyl-pyrazin-2-ylamine (0.40 g, 2.03 mmol) and CuI (catalytic amount) and stirred for 16 h at 80° C. The reaction mixture was cooled to RT, diluted with EtOAc (100 mL) and washed with water (50 mL). The organic layer was washed with brine solution (50 mL), dried over anhydrous Na2SO4 and solvent was evaporated under reduced pressure to afford crude product. The crude product was washed with diethyl ether to afford the title compound as a solid.

Workup

  1. temperatureThen the reaction mixture was cooled to room temperature
  2. stirringstirred for 16 h at 80° C
  3. temperatureThe reaction mixture was cooled to RT
  4. washwashed with water (50 mL)
  5. washThe organic layer was washed with brine solution (50 mL)
  6. dry with materialdried over anhydrous Na2SO4 and solvent
  7. customwas evaporated under reduced pressure
  8. customto afford crude product
  9. washThe crude product was washed with diethyl ether

Sources & evidence

ORD record
ord-a874897c6176456db24028d6aa2823b4
Source dataset
uspto-grants-2016_07
Patent number
US09393248B1

Reaction notes

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