N-Iodosuccinimide → 3,6-diethyl-N-(1-ethylpropyl)-5-iodopyrazin-2-amine

HRID 1063275노트

반응식

HRID 1063275 반응식
[CH2:1]([C:3]1[C:4]([NH:11][CH:12]([CH2:15][CH3:16])[CH2:13][CH3:14])=[N:5][C:6]([CH2:9][CH3:10])=[CH:7][N:8]=1)[CH3:2].C1C(=O)N([I:24])C(=O)C1>CN(C=O)C>[CH2:1]([C:3]1[C:4]([NH:11][CH:12]([CH2:15][CH3:16])[CH2:13][CH3:14])=[N:5][C:6]([CH2:9][CH3:10])=[C:7]([I:24])[N:8]=1)[CH3:2]

참가 물질

4

반응물 2

HCID 120273N-IodosuccinimideHCID 222787563,6-Diethyl-N-(pentan-3-yl)pyrazin-2-amine

생성물 1

HCID 222786973,6-diethyl-N-(1-ethylpropyl)-5-iodopyrazin-2-amine수율 74%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

A solution of 3,6-diethyl-N-(1-ethylpropyl)pyrazin-2-amine, NIS (5.37 g, 23.9 mmol) and anhydrous DMF (100 mL) under N2 was heated at 50° C. for 4 h. The solution was partitioned between ethyl acetate and H2O and separated. The aqueous phase was extracted with ethyl acetate and the combined organics were washed with H2O, brine and dried (MgSO4). The mixture was filtered and concentrated to give a brown oil which was purified by flash chromatography (20% ethyl acetate in heptane) to give 5.57 g (74%) of 3,6-diethyl-N-(1-ethylpropyl)-5-iodopyrazin-2-amine as a light brown oil. 1H NMR (400 MHz, CDCl3) δ 4.02 (m, 2 H), 2.76 (q, 2 H), 2.57 (q, 2 H), 1.60-1.70 (m, 2 H), 1.45-1.55 (m, 2 H) 1.20-1.30 (m, 6 H), 0.92 (q, 6 H).

후처리

  1. customThe solution was partitioned between ethyl acetate and H2O
  2. customseparated
  3. extractionThe aqueous phase was extracted with ethyl acetate
  4. washthe combined organics were washed with H2O, brine
  5. dry with materialdried (MgSO4)
  6. filtrationThe mixture was filtered
  7. concentrationconcentrated
  8. customto give a brown oil which
  9. customwas purified by flash chromatography (20% ethyl acetate in heptane)

출처 및 근거

ORD 기록
ord-a33b9554da2a4d299e46328b20aa4354
출처 데이터셋
uspto-grants-2005_11
특허 번호
US06964965B2

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