Sodium Hydroxide → HCID 22391941, compound

HRID 1072258Notes

Reaction equation

HRID 1072258 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]2[O:8][C:9]3[C:14]([CH2:15][C:5]2=[C:4]([NH2:17])[C:3]=1[C:18]#[N:19])=[CH:13][CH:12]=[CH:11][C:10]=3[OH:16].[OH-].[Na+]>CS(C)=O>[NH2:1][C:2]1[N:7]=[C:6]2[O:8][C:9]3[C:14]([CH2:15][C:5]2=[C:4]([NH2:17])[C:3]=1[C:18]#[N:19])=[CH:13][CH:12]=[CH:11][C:10]=3[OH:16].[C:9]1([OH:8])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 10422425HCID 10422425, compound

Product 1

HCID 22391941HCID 22391941, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
75 °C

Procedure

A solution of 2,4-diamino-9-hydroxy-5H-chromeno[2,3-b]pyridine-3-carbonitrile (0.73 mmol), and powdered sodium hydroxide (117 mg, 2.93 mmol)) in dimethyl sulfoxide (4 mL) is heated to 50° C. for five minutes. The corresponding halide is added and the reaction mixture is stirred at 50° C. or 75° C. until completion. The mixture is quenched with saturated aqueous ammonium chloride and directly purified by purified by reverse phase chromatography.

Workup

  1. customThe mixture is quenched with saturated aqueous ammonium chloride
  2. customdirectly purified
  3. customby purified by reverse phase chromatography

Sources & evidence

ORD record
ord-175f418ec9334386bafb1d7e30c280db
Source dataset
uspto-grants-2005_06
Patent number
US06909001B2

Reaction notes

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