Theophylline → 7-[4-(6-Chloronicotinoyl)benzyl]-1,3-dimethylxanthine

HRID 1291416ノート

反応式

HRID 1291416 の反応式
[CH3:1][N:2]1[C:11](=[O:12])[C:10]2[NH:9][CH:8]=[N:7][C:6]=2[N:5]([CH3:13])[C:3]1=[O:4].C(=O)([O-])[O-].[K+].[K+].[Cl:20][C:21]1[CH:36]=[CH:35][C:24]([C:25]([C:27]2[CH:34]=[CH:33][C:30]([CH2:31]Br)=[CH:29][CH:28]=2)=[O:26])=[CH:23][N:22]=1>CN(C=O)C.O>[Cl:20][C:21]1[CH:36]=[CH:35][C:24]([C:25]([C:27]2[CH:34]=[CH:33][C:30]([CH2:31][N:9]3[C:10]4[C:11](=[O:12])[N:2]([CH3:1])[C:3](=[O:4])[N:5]([CH3:13])[C:6]=4[N:7]=[CH:8]3)=[CH:29][CH:28]=2)=[O:26])=[CH:23][N:22]=1

参加物

6

反応物 3

HCID 2153TheophyllineHCID 11430Potassium CarbonateHCID 189188004-(6-Chloronicotinoyl)benzyl bromide

生成物 1

HCID 189188457-[4-(6-Chloronicotinoyl)benzyl]-1,3-dimethylxanthine収率 96.4%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

A solution of 1,3-dimethylxanthine (712 mg), potassium carbonate (578 mg) and 4-(6-chloronicotinoyl)benzyl bromide (1515 mg) in DMF (10 ml) was stirred at 60° C. for 5 hours. This reaction mixture was poured in water and extracted with ethyl acetate. The extract was washed with water, dried, and. concentrated. The residue was purified by silica gel column chromatography (hexane: ethyl acetate =1:3) and recrystallized from chloroform-isopropyl ether to provide the title compound as colorless solid (1562 mg).

後処理

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with water
  3. customdried
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel column chromatography (hexane: ethyl acetate =1:3)
  6. customrecrystallized from chloroform-isopropyl ether

出典と根拠

ORDレコード
ord-3be66d59852e4620ac6d8e241149b10e
出典データセット
uspto-grants-1998_05
特許番号
US05753664

反応ノート

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