Diisopropylethylamine → 1,1-Dimethylethyl 4-(5-iodo-2-pyrazinyl)-1-piperazinecarboxylate

HRID 2209272Notes

Reaction equation

HRID 2209272 reaction equation
Br[C:2]1[CH:7]=[N:6][C:5]([I:8])=[CH:4][N:3]=1.[N:9]1([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]1.CCN(C(C)C)C(C)C>CC(O)(C)C>[I:8][C:5]1[N:6]=[CH:7][C:2]([N:12]2[CH2:11][CH2:10][N:9]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:14][CH2:13]2)=[N:3][CH:4]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 143452tert-Butyl piperazine-1-carboxylateHCID 219312002-Bromo-5-iodopyrazine

Product 1

HCID 866692291,1-Dimethylethyl 4-(5-iodo-2-pyrazinyl)-1-piperazinecarboxylate

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Conditions

Temperature
100 °C

Procedure

2-bromo-5-iodopyrazine (503 mg, 1.77 mmol) and tert-butyl piperazine-1-carboxylate (355 mg, 1.91 mmol) were taken up in tBuOH (8 mL). iPr2NEt (400 μL, 2.3 mmol) was added and the stirred reaction mixture was heated to 100° C. After 66 h, the reaction mixture was cooled and was partitioned between EtOAc, water and brine. The phases were separated, and the organic phase was dried over Na2SO4, filtered, and concentrated. The crude residue was purified by silica gel chromatography (10-30% EtOAc in hexanes) to afford tert-butyl 4-(5-iodopyrazin-2-yl)piperazine-1-carboxylate 7.11.

Workup

  1. customthe stirred reaction mixture
  2. temperaturethe reaction mixture was cooled
  3. customwas partitioned between EtOAc, water and brine
  4. customThe phases were separated
  5. dry with materialthe organic phase was dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude residue was purified by silica gel chromatography (10-30% EtOAc in hexanes)

Sources & evidence

ORD record
ord-a53a06b1ed774fd19e6d7b53c443e10b
Source dataset
uspto-grants-2016_06
Patent number
US09376441B2

Reaction notes

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