Water → N-(4-iodophenyl)-N-isopropylpyrimidin-2-amine

HRID 230305

反応式

HRID 230305 の反応式
[I:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[N:14]=[CH:13][CH:12]=[CH:11][N:10]=2)=[CH:4][CH:3]=1.[H-].[Na+].I[CH:18]([CH3:20])[CH3:19].O>CN(C=O)C>[I:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]([CH:18]([CH3:20])[CH3:19])[C:9]2[N:10]=[CH:11][CH:12]=[CH:13][N:14]=2)=[CH:6][CH:7]=1

参加物

6

反応物 4

HCID 962WaterHCID 6362Isopropyl iodide2 回HCID 24758Sodium hydride2 回HCID 57762548N-(4-iodophenyl)pyrimidin-2-amine

生成物 1

HCID 57762606N-(4-iodophenyl)-N-isopropylpyrimidin-2-amine

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

実験手順

Under an argon atmosphere, a solution of N-(4-iodophenyl)pyrimidin-2-amine (8.00 g) in anhydrous DMF (50 ml) was added dropwise to a suspension of sodium hydride (1.08 g) in anhydrous DMF (200 ml), and the resulting mixture was stirred at room temperature for 80 minutes. To the reaction solution, 2-iodopropane (4.03 ml) was added, and the resulting mixture was stirred at room temperature for 2 hours. Sodium hydride (1.08 g) was added to the reaction solution and thereafter 2-iodopropane (4.03 ml) was added dropwise thereto, followed by stirring the resulting mixture at room temperature for 6 hours. Water was added to the reaction solution and the resulting mixture was extracted twice with ethyl acetate. Organic layers were washed 4 times with water and once with saturated brine, and dried over anhydrous sodium sulfate. After removing anhydrous sodium sulfate by filtration, the filtrate was concentrated. The residue was purified by column chromatography (silica gel, eluent: cyclohexane-cyclohexane/ethyl acetate=50/1). The obtained solid was recrystallized from hexane to obtain N-(4-iodophenyl)-N-isopropylpyrimidin-2-amine (7.06 g). NMR (H1, CDCl3): δ 1.14(3H, s), 1.16 (3H, s), 5.12-5.19 (1H, m), 6.52 (1H, t, J=4.6 Hz), 6.88-6.92 (2H, m), 7.74-7.77 (2H, m), 8.29 (2H, d, J=4.6 Hz)

後処理

  1. stirringthe resulting mixture was stirred at room temperature for 2 hours
  2. stirringby stirring the resulting mixture at room temperature for 6 hours
  3. extractionthe resulting mixture was extracted twice with ethyl acetate
  4. washOrganic layers were washed 4 times with water
  5. dry with materialonce with saturated brine, and dried over anhydrous sodium sulfate
  6. customAfter removing anhydrous sodium sulfate
  7. filtrationby filtration
  8. concentrationthe filtrate was concentrated
  9. customThe residue was purified by column chromatography (silica gel, eluent: cyclohexane-cyclohexane/ethyl acetate=50/1)
  10. customThe obtained solid was recrystallized from hexane

出典と根拠

ORDレコード
ord-1b8f67ee67524ab7b1f3d6c8e702e773
出典データセット
uspto-grants-2009_07
特許番号
US07566724B2

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