N-Iodosuccinimide → 5-(2-Amino-5-iodopyrimidin-4-yl)-2-(5-chloro-2-methylphenyl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrole-3-carboxamide

HRID 1403223ノート

反応式

HRID 1403223 の反応式
[I:1]N1C(=O)CCC1=O.[NH2:9][C:10]1[N:15]=[C:14]([C:16]2[N:20]([CH2:21][O:22][CH2:23][CH2:24][Si:25]([CH3:28])([CH3:27])[CH3:26])[C:19]([C:29]3[CH:34]=[C:33]([Cl:35])[CH:32]=[CH:31][C:30]=3[CH3:36])=[C:18]([C:37]([NH2:39])=[O:38])[CH:17]=2)[CH:13]=[CH:12][N:11]=1>CN(C=O)C.CCOC(C)=O>[NH2:9][C:10]1[N:15]=[C:14]([C:16]2[N:20]([CH2:21][O:22][CH2:23][CH2:24][Si:25]([CH3:27])([CH3:26])[CH3:28])[C:19]([C:29]3[CH:34]=[C:33]([Cl:35])[CH:32]=[CH:31][C:30]=3[CH3:36])=[C:18]([C:37]([NH2:39])=[O:38])[CH:17]=2)[C:13]([I:1])=[CH:12][N:11]=1

参加物

5

反応物 2

HCID 120273N-IodosuccinimideHCID 712396535-(2-aminopyrimidin-4-yl)-2-(5-chloro-2-methylphenyl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrole-3-carboxamide

生成物 1

HCID 712395925-(2-Amino-5-iodopyrimidin-4-yl)-2-(5-chloro-2-methylphenyl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrole-3-carboxamide収率 61.1%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
65 °C

実験手順

N-iodosuccinimide (720 mg, 3.2 mmol) was added to a solution of 5-(2-aminopyrimidin-4-yl)-2-(5-chloro-2-methylphenyl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrole-3-carboxamide (1.39 g, 3.0 mmol) in dry DMF (6 mL). The reaction mixture was heated at 65° C. for 7 h, allowed to cool to room temperature and then diluted with EtOAc (30 mL), washed with water (2×20 mL) brine, dried over sodium sulphate, and evaporated. The crude was purified by flash chromatography on silica gel (DCM/MeOH 97/3) to afford the title compound as yellow solid (1.07 g, 60%).

後処理

  1. temperatureto cool to room temperature
  2. washwashed with water (2×20 mL) brine
  3. dry with materialdried over sodium sulphate
  4. customevaporated
  5. customThe crude was purified by flash chromatography on silica gel (DCM/MeOH 97/3)

出典と根拠

ORDレコード
ord-698bfc98b8564d91ae1829eca2249f10
出典データセット
uspto-grants-2014_12
特許番号
US08912200B2

反応ノート

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