Sodium hydride → N-(4-iodophenyl)-N-(2-methoxyethyl)pyrimidin-2-amine

HRID 1360044ノート

反応式

HRID 1360044 の反応式
Br[CH2:2][CH2:3][O:4][CH3:5].[H-].[Na+].[I:8][C:9]1[CH:14]=[CH:13][C:12]([NH:15][C:16]2[N:21]=[CH:20][CH:19]=[CH:18][N:17]=2)=[CH:11][CH:10]=1>CN(C=O)C.[Cl-].[Na+].O>[I:8][C:9]1[CH:10]=[CH:11][C:12]([N:15]([CH2:2][CH2:3][O:4][CH3:5])[C:16]2[N:17]=[CH:18][CH:19]=[CH:20][N:21]=2)=[CH:13][CH:14]=1

参加物

6

反応物 3

HCID 24758Sodium hydrideHCID 809722-Bromoethyl methyl etherHCID 57762548N-(4-iodophenyl)pyrimidin-2-amine

生成物 1

HCID 57762539N-(4-iodophenyl)-N-(2-methoxyethyl)pyrimidin-2-amine

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 57417360Sodium chloride; water溶媒

実験手順

Under an argon atmosphere, 2-bromoethylmethyl ether (0.14 ml) and sodium hydride (48 mg) were added to a solution of N-(4-iodophenyl)pyrimidin-2-amine (300 mg) in anhydrous DMF (1 ml), 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, followed by drying the organic layer 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/chloroform=1/10) to obtain N-(4-iodophenyl)-N-(2-methoxyethyl)pyrimidin-2-amine (233 mg). NMR (H1, CDCl3): δ 3.32 (3H, s), 3.63 (2H, t, J=5.9 Hz), 4.14 (2H, t, J=5.9 Hz), 6.59 (1H, t, J=4.9 Hz), 7.09-7.13 (2H, m), 7.70-7.73 (2H, m), 8.32 (2H, d, J=4.9 Hz)

後処理

  1. extractionthe resulting mixture was extracted with chloroform
  2. dry with materialby drying the organic layer over anhydrous sodium sulfate
  3. customAfter removing anhydrous sodium sulfate
  4. filtrationby filtration
  5. concentrationthe filtrate was concentrated
  6. customThe residue was purified by column chromatography (silica gel, eluent:hexane/chloroform=1/10)

出典と根拠

ORDレコード
ord-2d0a123732734fd38e3e69a597ef40d5
出典データセット
uspto-grants-2011_02
特許番号
US07879837B2

反応ノート

読み込み中…