Sulfuric Acid → 5-(3-Fluoropyridin-4-yl)-6-pyridin-3-ylpyrazin-2(1H)-one

HRID 1710689Notes

Reaction equation

HRID 1710689 reaction equation
N([O-])=O.[Na+].[F:5][C:6]1[CH:7]=[N:8][CH:9]=[CH:10][C:11]=1[C:12]1[N:13]=[CH:14][C:15](N)=[N:16][C:17]=1[C:18]1[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=1.S(=O)(=O)(O)[OH:26].[OH-].[Na+]>O>[F:5][C:6]1[CH:7]=[N:8][CH:9]=[CH:10][C:11]=1[C:12]1[N:13]=[CH:14][C:15](=[O:26])[NH:16][C:17]=1[C:18]1[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=1

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 160708355-(3-Fluoropyridin-4-yl)-6-pyridin-3-ylpyrazin-2-amineHCID 23668193Sodium Nitrite

Product 1

HCID 594575875-(3-Fluoropyridin-4-yl)-6-pyridin-3-ylpyrazin-2(1H)-oneYield 99%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of sodium nitrite (0.248 g, 3.6 mmol) in water (2.5 mL) was added dropwise to a stirred, cooled (ice-bath) mixture of 5-(3-fluoropyridin-4-yl)-6-pyridin-3-ylpyrazin-2-amine (Example 115) (0.80 g, 3.0 mmol) and 5% aqueous sulphuric acid (18 mL). After 1 hour, the mixture was taken to pH 5-6 with aqueous sodium hydroxide solution with external cooling. The mixture was concentrated to low bulk then extracted with chloroform. The organic layer was dried (MgSO4) and concentrated in vaccuo to give the title compound (0.793 g, 99%) as a white solid.

Workup

  1. temperaturecooled
  2. concentrationThe mixture was concentrated to low bulk
  3. extractionthen extracted with chloroform
  4. dry with materialThe organic layer was dried (MgSO4)
  5. concentrationconcentrated in vaccuo

Sources & evidence

ORD record
ord-def634f271d246eda9cb6a25def3a646
Source dataset
uspto-grants-2010_09
Patent number
US07790728B2

Reaction notes

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