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

HRID 1046564
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HRID 1046564 반응식
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
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참가 물질

8

반응물 3

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

생성물 1

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

시약·촉매·용매 4

HCID 962Water용매2회
HCID 6228
Dimethylformamide
용매
HCID 8857Ethyl Acetate용매
HCID 57417360Sodium chloride; water용매

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온도
90 °C

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-9c17cfbe330e4899bd97559dfd7b4eaf
출처 데이터셋
uspto-grants-2013_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08569337B2

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