Isobutyraldehyde → 6-Chloro-3-isopropyl-[1,2,4]triazolo[4,3-a]pyrazine

HRID 1930074Notes

Reaction equation

HRID 1930074 reaction equation
[Cl:1][C:2]1[CH:7]=[N:6][C:5]([NH:8][NH2:9])=[CH:4][N:3]=1.[CH:10](=O)[CH:11]([CH3:13])[CH3:12].C(O)(=O)C.C(O)(=O)C.IC1C=CC=CC=1>C(Cl)Cl>[Cl:1][C:2]1[N:3]=[CH:4][C:5]2[N:6]([C:10]([CH:11]([CH3:13])[CH3:12])=[N:9][N:8]=2)[CH:7]=1

Participants

5

Reactant 3

HCID 6561IsobutyraldehydeHCID 12217721Iodo benzene diacetateHCID 158645972-Chloro-5-hydrazinylpyrazine

Product 1

HCID 579299536-Chloro-3-isopropyl-[1,2,4]triazolo[4,3-a]pyrazineYield 63%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

The 2-chloro-5-hydrazinylpyrazine (0.325 g, 2.248 mmol) was suspended in DCM (4 mL) then the isobutyraldehyde (0.195 g, 2.70 mmol) was added. The mixture was stirred for about 30 min, the solvent was concentrated under reduced pressure and the solid was dissolved in DCM (4 mL). Iodobenzene diacetate (0.724 g, 2.24 mmol) was added and the solution was stirred at ambient temperature for about 2 h. The mixture was diluted with DCM (20 mL), extracted with saturated aqueous NaHCO3, dried over MgSO4, filtered and concentrated under reduced pressure. The material was purified by flash chromatography on silica gel using DCM/EtOAc (1:1) as an eluent to give the title compound (0.278 g, 63%): LC/MS (Table 1, Method g) Rt=1.74 min; MS m/z: 197.1 (M+H)+.

Workup

  1. concentrationthe solvent was concentrated under reduced pressure
  2. dissolutionthe solid was dissolved in DCM (4 mL)
  3. stirringthe solution was stirred at ambient temperature for about 2 h
  4. extractionextracted with saturated aqueous NaHCO3
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe material was purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-0ea8c00f8abc44d5a693c652c258ff6d
Source dataset
uspto-grants-2012_05
Patent number
US08188083B2

Reaction notes

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