Methyl chloroacetate → 2-(Chloromethyl)-5,8-dimethyl-[1,2,4]triazolo[1,5-a]pyrazine

HRID 1771997ノート

反応式

HRID 1771997 の反応式
[NH2:1][N:2]1[C:7]([CH3:8])=[CH:6][N:5]=[C:4]([CH3:9])[C:3]1=[NH2+:10].CC1C=C(C)C=C(C)C=1S([O-])(=O)=O.[OH-].[Na+].[Cl:26][CH2:27][C:28](OC)=O>CCO>[Cl:26][CH2:27][C:28]1[N:10]=[C:3]2[C:4]([CH3:9])=[N:5][CH:6]=[C:7]([CH3:8])[N:2]2[N:1]=1

参加物

5

反応物 3

HCID 7295Methyl chloroacetateHCID 14798Sodium HydroxideHCID 178425979HCID 178425979、化合物

生成物 1

HCID 591512352-(Chloromethyl)-5,8-dimethyl-[1,2,4]triazolo[1,5-a]pyrazine収率 36.3%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

反応条件

温度
60 °C

実験手順

A mixture of 1-amino-3,6-dimethylpyrazin-2(1H)-iminium-2,4,6-trimethylbenzenesulfonate (2.0 g, 5.9 mmol) and NaOH (480 mg, 12 mmol) in EtOH (20 mL) was stirred at 60° C. for 1 h. Methyl 2-chloroacetate (1.34 g, 12.4 mmol) was then added slowly. The reaction mixture was refluxed for 4 h, then the solvent was removed. The product was purified by silica gel column chromatography to give 2-(chloromethyl)-5,8-dimethyl-[1,2,4]triazolo[1,5-a]pyrazine as a yellow solid (420 mg, yield 36.3%). ESI MS: m/z 197 [M+1]+.

後処理

  1. temperatureThe reaction mixture was refluxed for 4 h
  2. customthe solvent was removed
  3. customThe product was purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-d7125943e5c745979c35f767be1f14a1
出典データセット
uspto-grants-2016_02
特許番号
US09249162B2

反応ノート

読み込み中…