Sodium hydride → 5-[2-(1,3-Dioxolan-2-yl)ethyl]-3-methoxypyrido[2,3-b]pyrazin-6 (5H)-one

HRID 1847015

Reaction equation

HRID 1847015 reaction equation
[CH3:1][O:2][C:3]1[N:8]=[C:7]2[NH:9][C:10](=[O:13])[CH:11]=[CH:12][C:6]2=[N:5][CH:4]=1.[Br-].[Li+].[H-].[Na+].Br[CH2:19][CH2:20][CH:21]1[O:25][CH2:24][CH2:23][O:22]1>CN(C)C=O.O>[O:22]1[CH2:23][CH2:24][O:25][CH:21]1[CH2:20][CH2:19][N:9]1[C:7]2=[N:8][C:3]([O:2][CH3:1])=[CH:4][N:5]=[C:6]2[CH:12]=[CH:11][C:10]1=[O:13]

Participants

7

Reactant 4

HCID 24758Sodium hydrideHCID 82050Lithium BromideHCID 877762-(2-Bromoethyl)-1,3-dioxolaneHCID 578153663-Methoxypyrido[2,3-b]pyrazin-6(5H)-one

Product 1

HCID 867249455-[2-(1,3-Dioxolan-2-yl)ethyl]-3-methoxypyrido[2,3-b]pyrazin-6 (5H)-one

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

3-Methoxypyrido[2,3-b]pyrazin-6(5H)-one (400 mg, 2.26 mmol) was dissolved in N,N-dimethylformamide (12 ml). Lithium bromide (206 mg, 2.37 mmol) and sodium hydride (55%, 104 mg, 2.37 mmol) were added to the solution under cooling on ice and stirred for one and a half hours while the temperature of the reaction solution was raised to room temperature. The reaction solution was cooled on ice again, 2-(2-bromoethyl)-1,3-dioxolane (0.345 mmol, 2.94 mmol) was added thereto and the mixture was stirred at room temperature for 22 hours. Water was added to the reaction solution, which was then extracted with ethyl acetate and washed with saturated sodium chloride solution. After drying over anhydrous sodium sulfate, the solvent was removed under reduced pressure. The residue was purified by silica gel column chromatography (chloroform/methanol) to yield 731 mg (quantitative) of the title compound in the form of a yellow oily product.

Workup

  1. temperatureunder cooling on ice
  2. temperatureThe reaction solution was cooled on ice again
  3. stirringthe mixture was stirred at room temperature for 22 hours
  4. extractionwas then extracted with ethyl acetate
  5. washwashed with saturated sodium chloride solution
  6. dry with materialAfter drying over anhydrous sodium sulfate
  7. customthe solvent was removed under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (chloroform/methanol)

Sources & evidence

ORD record
ord-26d43389f48840b1a74a3c4a2c19934a
Source dataset
uspto-grants-2015_02
Patent number
US08952010B2

Linked notes

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