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

HRID 1063275ノート

反応式

HRID 1063275 の反応式
[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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-a33b9554da2a4d299e46328b20aa4354
出典データセット
uspto-grants-2005_11
特許番号
US06964965B2

反応ノート

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