Water → HCID 57815388, compound

HRID 1510634Notes

Reaction equation

HRID 1510634 reaction equation
[NH2:1][C:2]1[C:3]([NH:8][CH2:9][CH:10]2[O:14][CH2:13][CH2:12][O:11]2)=[N:4][CH:5]=[CH:6][CH:7]=1.C1(C)C=CC=CC=1.[O:22]=[CH:23][C:24](OCC)=O.O>C(O)C.C(OCC)(=O)C>[O:11]1[CH2:12][CH2:13][O:14][CH:10]1[CH2:9][N:8]1[C:23](=[O:22])[CH:24]=[N:1][C:2]2[CH:7]=[CH:6][CH:5]=[N:4][C:3]1=2

Participants

7

Reactant 4

HCID 962WaterHCID 1140TolueneHCID 70211Ethyl oxoacetateHCID 57815317HCID 57815317, compound

Product 1

HCID 57815388HCID 57815388, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 0.20 g of 3-amino-2-(1,3-dioxolan-2-ylmethyl)aminopyridine in 2 mL of ethanol, 0.25 g of a 45 to 50% toluene solution of ethyl oxoacetate was added, and the mixture was heated under reflux while stirring for 1 hour 30 minutes. The reaction mixture was cooled to room temperature, and thereto were added water and ethyl acetate. 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 chloroform:methanol=100:0 to 90:10 to obtain 0.16 g of 4-(1,3-dioxolan-2-ylmethyl)pyrido(2,3-b)pyrazin-3(4H)-one as a light brown solid.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux
  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 chloroform

Sources & evidence

ORD record
ord-876a6cd296ea4f93b622edc6ea3aff86
Source dataset
uspto-grants-2012_07
Patent number
US08211908B2

Reaction notes

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