Toluene → 4-((1,3-Dioxolan-2-yl)methyl)-6-methoxypyrido[3,2-b]pyrazin-3(4h)-one

HRID 385499Notes

Reaction equation

HRID 385499 reaction equation
[NH2:1][C:2]1[C:3]([NH:10][CH2:11][CH:12]2[O:16][CH2:15][CH2:14][O:13]2)=[N:4][C:5]([O:8][CH3:9])=[CH:6][CH:7]=1.C1(C)C=CC=CC=1.[O:24]=[CH:25][C:26](OCC)=O.[H-].[Na+]>O1CCOCC1.C(OCC)(=O)C.O>[O:13]1[CH2:14][CH2:15][O:16][CH:12]1[CH2:11][N:10]1[C:25](=[O:24])[CH:26]=[N:1][C:2]2[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[N:4][C:3]1=2

Participants

8

Reactant 4

HCID 1140TolueneHCID 24758Sodium hydrideHCID 70211Ethyl oxoacetateHCID 578153463-Amino-2-(1,3-dioxolan-2-ylmethyl)amino-6-methoxypyridine

Product 1

HCID 578152174-((1,3-Dioxolan-2-yl)methyl)-6-methoxypyrido[3,2-b]pyrazin-3(4h)-one

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 0.20 g of 3-amino-2-(1,3-dioxolan-2-ylmethyl)amino-6-methoxypyridine in 2 mL of dioxane, 0.22 g of a 45 to 50% toluene solution of ethyl oxoacetate was added, and the mixture was stirred at room temperature for 2 hours and then left overnight. Thereto was added 36 mg of 60% sodium hydride, and the mixture was stirred at room temperature for 30 minutes. To the reaction mixture, water and ethyl acetate were added. 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 with 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 flash silica gel column chromatography using gradient elution with hexane:ethyl acetate=100:0 to 50:50 to obtain 36 mg of 4-(1,3-dioxolan-2-ylmethyl)-6-methoxypyrido (2,3-b)pyrazin-3(4H)-one as a light brown solid.

Workup

  1. waitleft overnight
  2. stirringthe mixture was stirred at room temperature for 30 minutes
  3. customThe organic layer was separated
  4. extractionthe aqueous layer was extracted with ethyl acetate
  5. washthe resultant solution was washed with a saturated aqueous sodium chloride solution
  6. dry with materialdried over anhydrous magnesium sulfate
  7. distillationthe solvent was distilled off under reduced pressure
  8. customThe resultant residue was purified by flash silica gel column chromatography
  9. washelution with hexane

Sources & evidence

ORD record
ord-60df9fe899074dd196abf361c5b00c43
Source dataset
uspto-grants-2013_02
Patent number
US08367831B2

Reaction notes

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