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

HRID 2170142Notes

Reaction equation

HRID 2170142 reaction equation
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

Participants

3

Reactant 2

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

Product 1

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

Conditions

Temperature
110 °C

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-09ac7eee98a24cecbfeb1f9146261945
Source dataset
uspto-grants-2015_06
Patent number
US09050345B2

Reaction notes

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