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

HRID 1360045

반응식

HRID 1360045 반응식
[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

참가 물질

6

반응물 4

HCID 962WaterHCID 6362Isopropyl iodide2회HCID 24758Sodium hydride2회HCID 57762548N-(4-iodophenyl)pyrimidin-2-amine

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

실험 절차

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)

후처리

  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

출처 및 근거

ORD 기록
ord-41fcd728dad54ee68126fd5f83d16eb0
출처 데이터셋
uspto-grants-2011_02
특허 번호
US07879837B2

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