2-Hydrazinopyrazine → 2-[5-(4-Fluorophenyl)-3-isopropyl-1H-pyrazol-1-YL]pyrazine

HRID 1029463Notes

Reaction equation

HRID 1029463 reaction equation
[NH:1]([C:3]1[CH:8]=[N:7][CH:6]=[CH:5][N:4]=1)[NH2:2].[F:9][C:10]1[CH:15]=[CH:14][C:13]([C:16](=O)[CH2:17][C:18](=O)[CH:19]([CH3:21])[CH3:20])=[CH:12][CH:11]=1>C(O)(=O)C>[F:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[N:1]([C:3]3[CH:8]=[N:7][CH:6]=[CH:5][N:4]=3)[N:2]=[C:18]([CH:19]([CH3:21])[CH3:20])[CH:17]=2)=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 14878232-HydrazinopyrazineHCID 141543761-(4-Fluorophenyl)-4-methylpentane-1,3-dione

Product 1

HCID 148513072-[5-(4-Fluorophenyl)-3-isopropyl-1H-pyrazol-1-YL]pyrazineYield 62.1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

The hydrazino pyrazine (20.20 g, 183 mmol, prepared as in J. Orq. Chem., 27, 3243 (1962)) was added in portions to the 1,3-diketone (34.7 g, 167 mmol, prepared in Example 1, Step A) in glacial acetic acid (400 mL). The reaction was refluxed for 2 hours, concentrated, and partitioned between EtOAc and K2CO3 (aq). The organics were dried (MgSO4) and evaporated to give a brown solid. Recrystallization from hexanes afforded 29.27 g (62%) of a cream colored solid.

Workup

  1. temperatureThe reaction was refluxed for 2 hours
  2. concentrationconcentrated
  3. custompartitioned between EtOAc and K2CO3 (aq)
  4. dry with materialThe organics were dried (MgSO4)
  5. customevaporated
  6. customto give a brown solid
  7. customRecrystallization from hexanes

Sources & evidence

ORD record
ord-d364192948fb4d1f84609591d2370784
Source dataset
uspto-grants-1992_04
Patent number
US05102893

Reaction notes

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