Ammonium Hydroxide → 5-phenylpyrrolo[2,1-f][1,2,4]triazine-2,4(1H,3H)-dione

HRID 2170142ノート

反応式

HRID 2170142 の反応式
C([O:3][C:4]([NH:6][N:7]1[CH:11]=[CH:10][C:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[C:8]1[C:18]([O:20]C)=O)=O)C.[OH-].[NH4+:23]>>[C:12]1([C:9]2[CH:10]=[CH:11][N:7]3[C:8]=2[C:18](=[O:20])[NH:23][C:4](=[O:3])[NH:6]3)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

参加物

3

反応物 2

HCID 14923Ammonium HydroxideHCID 90386155methyl 1-((ethoxycarbonyl)amino)-3-phenyl-1H-pyrrole-2-carboxylate

生成物 1

HCID 903861165-phenylpyrrolo[2,1-f][1,2,4]triazine-2,4(1H,3H)-dione収率 38.1%

反応条件

温度
110 °C

実験手順

Methyl 1-((ethoxycarbonyl)amino)-3-phenyl-1H-pyrrole-2-carboxylate (1.00 g, 3.47 mmol) was taken in a pressure tube and ammonium hydroxide (30%, 67.5 mL, 1.73 mol) was added and sealed. The reaction mixture was stirred at 110° C. for 30 h and transferred to a round bottomed flask and concentrated under reduced pressure. Toluene was added to it and azeotroped to remove trace amount of water (3 times). Then residue obtained was triturated with ethyl acetate (50×2 mL) to afford 5-phenylpyrrolo[2,1-f][1,2,4]triazine-2,4(1H,3H)-dione (0.300 g, 38.1%). LCMS Condition B-39: retention time 1.49 min, [M+1]=228.0.

後処理

  1. customsealed
  2. customtransferred to a round bottomed flask
  3. concentrationconcentrated under reduced pressure
  4. additionToluene was added to it
  5. customazeotroped
  6. customto remove trace amount of water (3 times)
  7. customThen residue obtained
  8. customwas triturated with ethyl acetate (50×2 mL)

出典と根拠

ORDレコード
ord-09ac7eee98a24cecbfeb1f9146261945
出典データセット
uspto-grants-2015_06
特許番号
US09050345B2

反応ノート

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