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

HRID 717583Notes

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-aec93e1700404bd8a582e5e90557ca81
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09193722B2

Reaction notes

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