Methanol → 4-Chloro-2-[1,2,4]triazolo[4,3-a]pyrimidin-3-yl-phenylamine

HRID 2238314ノート

反応式

HRID 2238314 の反応式
[NH:1]([C:3]1[N:8]=[CH:7][CH:6]=[CH:5][N:4]=1)[NH2:2].[N+:9]([C:12]1[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][C:13]=1[CH:14]=O)([O-])=O.CO.C(O)(=O)C.C(O)(=O)C.IC1C=CC=CC=1>[NH4+].[Cl-].CCO.[Fe]>[Cl:20][C:17]1[CH:18]=[CH:19][C:12]([NH2:9])=[C:13]([C:14]2[N:4]3[CH:5]=[CH:6][CH:7]=[N:8][C:3]3=[N:1][N:2]=2)[CH:16]=1

参加物

8

反応物 4

HCID 887MethanolHCID 811235-Chloro-2-nitrobenzaldehydeHCID 3465582-HydrazinylpyrimidineHCID 12217721Iodo benzene diacetate

生成物 1

HCID 436286444-Chloro-2-[1,2,4]triazolo[4,3-a]pyrimidin-3-yl-phenylamine

試薬・触媒・溶媒 3

HCID 23925Iron触媒HCID 702Ethanol溶媒HCID 25517Ammonium Chloride溶媒

反応条件

温度
60 °C

実験手順

A 5 mL scintillation vial was charged with 2-hydrazinopyrimidine (61 mg, 0.55 mmol), 2-nitro-5-chlorobenzaldehyde (112 mg, 0.06 mmol) and MeOH (500 μL) and heated to 60° C. for 30 minutes. The MeOH was then removed in vacuo and the resultant solid was washed with Et2O. The crude solid (30 mg) was then suspended in CH2Cl2 (1 mL) and iodobenzene diacetate (39 mg, 0.12 mmol) was added. The reaction was stirred at room temperature for 30 minutes after which the solvent was removed in vacuo. The resultant residue was then dissolved in a 10% solution of saturated NH4Cl(aq) in EtOH and iron (19 mg, 0.33 mmol) was then added and the reaction was stirred at 80° C. for 4 h. The solvent was then removed in vacuo and the product was purified by silica gel chromatography to afford 4-chloro-2-[1,2,4]triazolo[4,3-a]pyrimidin-3-yl-phenylamine as a light yellow oil.

後処理

  1. customThe MeOH was then removed in vacuo
  2. washthe resultant solid was washed with Et2O
  3. customwas removed in vacuo
  4. additionwas then added
  5. stirringthe reaction was stirred at 80° C. for 4 h
  6. customThe solvent was then removed in vacuo
  7. customthe product was purified by silica gel chromatography

出典と根拠

ORDレコード
ord-f29e76e1952b4394943992fe5108c5a9
出典データセット
uspto-grants-2010_05
特許番号
US07718683B2

反応ノート

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