Acetic Acid → 2-(5-Bromo-2-fluoro-phenyl)-3H-pteridin-4-one

HRID 928262Notes

Reaction equation

HRID 928262 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:20])=[C:6]([CH:19]=1)[C:7]([NH:9][C:10]1[C:11]([C:16]([NH2:18])=[O:17])=[N:12][CH:13]=[CH:14][N:15]=1)=O.[OH-].[K+].CC(O)=O>O.CS(C)=O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:20])=[C:6]([C:7]2[NH:18][C:16](=[O:17])[C:11]3[C:10](=[N:15][CH:14]=[CH:13][N:12]=3)[N:9]=2)[CH:19]=1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 14797Potassium HydroxideHCID 577423843-(5-Bromo-2-fluorobenzoylamino)pyrazine-2-carboxamide

Product 1

HCID 1361099582-(5-Bromo-2-fluoro-phenyl)-3H-pteridin-4-oneYield 84.1%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

A mixture of 3-(5-bromo-2-fluorobenzoylamino)pyrazine-2-carboxamide 103 (2.3 g, 6.78 mmol) and KOH (3.81 g, 67.8 mmol) in H2O (60 mL) and DMSO (20 mL) was stirred at room temperature for 45 min. Acidification to pH 5 (pH paper control) with AcOH followed by addition of 50 mL of ice-cold water afforded a precipitate, which was filtered off, washed with H2O, acetonitrile and ether to give 1.83 g of the title product 104 as a white powder (LCMS analysis).

Workup

  1. customafforded a precipitate, which
  2. filtrationwas filtered off
  3. washwashed with H2O, acetonitrile and ether

Sources & evidence

ORD record
ord-9941235d6e0b4118a1762ec6c242905a
Source dataset
uspto-grants-2016_03
Patent number
US09290502B2

Reaction notes

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