Sodium hydride → (4-Acetoxybenzyl)-(4-iodophenyl)pyrimidin-2-ylamine

HRID 1752056

반응식

HRID 1752056 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+].[C:17]([O:20][C:21]1[CH:28]=[CH:27][C:24]([CH2:25]Cl)=[CH:23][CH:22]=1)(=[O:19])[CH3:18]>CN(C=O)C.[Cl-].[Na+].O>[C:17]([O:20][C:21]1[CH:28]=[CH:27][C:24]([CH2:25][N:8]([C:5]2[CH:4]=[CH:3][C:2]([I:1])=[CH:7][CH:6]=2)[C:9]2[N:10]=[CH:11][CH:12]=[CH:13][N:14]=2)=[CH:23][CH:22]=1)(=[O:19])[CH3:18]

참가 물질

6

반응물 3

HCID 24758Sodium hydrideHCID 1483124-(Chloromethyl)phenyl acetateHCID 57762548N-(4-iodophenyl)pyrimidin-2-amine

생성물 1

HCID 57762581(4-Acetoxybenzyl)-(4-iodophenyl)pyrimidin-2-ylamine

시약·촉매·용매 2

HCID 6228Dimethylformamide용매3회HCID 57417360Sodium chloride; water용매

실험 절차

Under an argon atmosphere, a solution of N-(4-iodophenyl)pyrimidin-2-amine (68 mg) in anhydrous DMF (1.0 ml) was added dropwise to a solution of sodium hydride (16 mg) in anhydrous DMF (1.0 ml), and the resulting mixture was stirred at room temperature for 30 minutes. To the reaction solution, a solution of 4-acetoxybenzyl chloride (0.04 ml) in anhydrous DMF (0.5 ml) was added, and the resulting mixture was stirred at room temperature overnight. Saturated brine was added to the reaction solution and the resulting mixture was extracted with chloroform. Organic layer was 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: hexane/ethyl acetate=6/1) to obtain (4-acetoxybenzyl)-(4-iodophenyl)pyrimidin-2-ylamine (67 mg). NMR (H1, CDCl3): δ 2.28 (3H, s), 5.22 (2H, s), 6.63 (1H, t, J=4.6 Hz), 6.98-7.02 (4H, m), 7.26 (2H, d, J=8.1 Hz), 7.64-7.67 (2H, m), 8.34 (2H, d, J=4.6 Hz)

후처리

  1. stirringthe resulting mixture was stirred at room temperature overnight
  2. extractionthe resulting mixture was extracted with chloroform
  3. dry with materialOrganic layer was dried over anhydrous sodium sulfate
  4. customAfter removing anhydrous sodium sulfate
  5. filtrationby filtration
  6. concentrationthe filtrate was concentrated
  7. customThe residue was purified by column chromatography (silica gel, eluent: hexane/ethyl acetate=6/1)

출처 및 근거

ORD 기록
ord-687fa629c8f64005b403a98b7d1d8f48
출처 데이터셋
uspto-grants-2015_10
특허 번호
US09162988B2

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