Potassium Carbonate → HCID 86695561, compound

HRID 1425760Notes

Reaction equation

HRID 1425760 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([O:9][CH3:10])=[CH:5][N:4]=1.[OH:11][C:12]1[CH:17]=[C:16]([OH:18])[CH:15]=[CH:14][N:13]=1.C([O-])([O-])=O.[K+].[K+]>C(#N)C.CN(C=O)C.O>[CH3:10][O:9][C:6]1[CH:7]=[CH:8][C:3]([CH2:2][O:18][C:16]2[CH:15]=[CH:14][NH:13][C:12](=[O:11])[CH:17]=2)=[N:4][CH:5]=1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 113331432-(Bromomethyl)-5-methoxypyridineHCID 178516518HCID 178516518, compound

Product 1

HCID 86695561HCID 86695561, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 2-bromomethyl-5-methoxy-pyridine (preparation 11a, 2.00 g crude material), 2,4-dihydroxypyridine (1.06 g, 9.5 mmol) in acetonitrile (20 mL) and DMF (5 mL) is added K2CO3 and the mixture is stirred for 4 h at 50° C. and overnight at room temperature. The reaction mixture is diluted with water (60 mL) and extracted several times with ethyl acetate. The organic layer is dried over Na2SO4, concentrated under reduced pressure and purified via reverse phase HPLC chromatography (Waters XBridge 5 μm, gradient 25%→95% methanol in water+0.3% NH4OH).

Workup

  1. extractionextracted several times with ethyl acetate
  2. dry with materialThe organic layer is dried over Na2SO4
  3. concentrationconcentrated under reduced pressure
  4. custompurified via reverse phase HPLC chromatography (Waters XBridge 5 μm, gradient 25%→95% methanol in water+0.3% NH4OH)

Sources & evidence

ORD record
ord-a28f39d34a6f40ae8f0d37ce17c5d61a
Source dataset
uspto-grants-2015_01
Patent number
US08933079B2

Reaction notes

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