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Potassium Carbonate → (S)-tert-butyl 4-(6-iodopyrazin-2-yl)-2-isobutylpiperazine-1-carboxylate

HRID 1046564
Notes
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Reaction equation

HRID 1046564 reaction equation
I[C:2]1[CH:7]=[N:6][CH:5]=[C:4]([I:8])[N:3]=1.[CH2:9]([C@H:13]1[CH2:18][NH:17][CH2:16][CH2:15][N:14]1[C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH:10]([CH3:12])[CH3:11].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.C(OCC)(=O)C.O.[Cl-].[Na+].O>[I:8][C:4]1[N:3]=[C:2]([N:17]2[CH2:16][CH2:15][N:14]([C:19]([O:21][C:22]([CH3:23])([CH3:24])[CH3:25])=[O:20])[C@@H:13]([CH2:9][CH:10]([CH3:12])[CH3:11])[CH2:18]2)[CH:7]=[N:6][CH:5]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 3

HCID 11430Potassium CarbonateHCID 110020782,6-DiiodopyrazineHCID 177504371,1-Dimethylethyl (2S)-2-(2-methylpropyl)-1-piperazinecarboxylate

Product 1

HCID 86665931(S)-tert-butyl 4-(6-iodopyrazin-2-yl)-2-isobutylpiperazine-1-carboxylateYield 78.1%

Reagents, catalysts & solvents 4

HCID 962Water
Solvent
2×
HCID 6228DimethylformamideSolvent
HCID 8857Ethyl AcetateSolvent
HCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 2,6-diiodopyrazine (1 g, 3.013 mmol), tert-butyl (2S)-2-isobutylpiperazine-1-carboxylate (949.3 mg, 3.917 mmol) and K2CO3 (624.7 mg, 4.520 mmol) in DMF (5 mL) was heated to 90° C. and stirred for 17 hrs. It was then allowed to cool and diluted with ethyl acetate and water, further washed organic layer with water and brine, dried (MgSO4) and concentrated to give an orange oil. It was then columned on silica gel eluting with 1:1 EtOAc/hexanes to give (S)-tert-butyl 4-(6-iodopyrazin-2-yl)-2-isobutylpiperazine-1-carboxylate as a yellow oil 1.05 g, 78%). ES+ 447. 1HNMR (CDCl3) 0.98 (6H, d), 1.23-1.45 (2H, m), 1.55-1.63 (1H, m), 2.91-3.00 (1H, m), 3.03-3.21 (2H, m), 3.98-4.20 (3H, m), 4.25 (1H, brs), 7.95 (1H, s), 8.06 (1H, s).

Workup

  1. temperatureto cool
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated
  4. customto give an orange oil

Sources & evidence

ORD record
ord-9c17cfbe330e4899bd97559dfd7b4eaf
Source dataset
uspto-grants-2013_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08569337B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes