Water → 4-(1,3-dioxolan-2-ylmethyl)-6-fluoropyrido(2,3-b)pyrazin-3(4H)-one

HRID 1510641Notes

Reaction equation

HRID 1510641 reaction equation
Cl[C:2]1[CH:3]=[CH:4][C:5]2[N:10]=[CH:9][C:8](=[O:11])[N:7]([CH2:12][CH:13]3[O:17][CH2:16][CH2:15][O:14]3)[C:6]=2[N:18]=1.[F-:19].[Cs+].C(OCC)(=O)C.O>CN(C)C=O>[O:14]1[CH2:15][CH2:16][O:17][CH:13]1[CH2:12][N:7]1[C:8](=[O:11])[CH:9]=[N:10][C:5]2[CH:4]=[CH:3][C:2]([F:19])=[N:18][C:6]1=2

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 25953Cesium fluoride2×HCID 578153306-Chloro-4-(1,3-dioxolan-2-ylmethyl)pyrido[2,3-b]pyrazin-3(4h)-one

Product 1

HCID 578154664-(1,3-dioxolan-2-ylmethyl)-6-fluoropyrido(2,3-b)pyrazin-3(4H)-oneYield 63.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
95 °C

Procedure

To a solution of 0.10 g of 6-chloro-4-(1,3-dioxolan-2-ylmethyl)pyrido(2,3-b)pyrazin-3(4H)-one in 3 mL of N,N-dimethylformamide, 0.57 g of cesium fluoride was added, and the mixture was stirred at 90 to 100° C. for 1 hour 10 minutes. Thereto was further added 0.57 g of cesium fluoride, and the mixture was stirred at 90 to 100° C. for 1 hour 30 minutes. Thereto were added ethyl acetate and water, the organic layer was separated, and the aqueous layer was extracted with ethyl acetate. The organic layer and the extract were combined, the resultant solution was washed sequentially with diluted hydrochloric acid and a saturated aqueous sodium chloride solution, and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The resultant residue was purified by silica gel column chromatography using an eluent of chloroform:methanol=50:1 to obtain 60 mg of 4-(1,3-dioxolan-2-ylmethyl)-6-fluoropyrido(2,3-b)pyrazin-3(4H)-one as a light yellow solid.

Workup

  1. stirringthe mixture was stirred at 90 to 100° C. for 1 hour 30 minutes
  2. customthe organic layer was separated
  3. extractionthe aqueous layer was extracted with ethyl acetate
  4. washthe resultant solution was washed sequentially with diluted hydrochloric acid
  5. dry with materiala saturated aqueous sodium chloride solution, and dried over anhydrous magnesium sulfate
  6. distillationthe solvent was distilled off under reduced pressure
  7. customThe resultant residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-ef9da71872c0414a97e3625eb2abed1a
Source dataset
uspto-grants-2012_07
Patent number
US08211908B2

Reaction notes

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