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

HRID 1046564Notes

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

Participants

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

temperatureto cool
dry with materialdried (MgSO4)
concentrationconcentrated
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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