Potassium Carbonate → 6-Methoxy-4-{2-[(2R)-oxiran-2-yl]ethyl}pyrido[2,3-b]pyrazin-3(4H)-one

HRID 1847072Notes

Reaction equation

HRID 1847072 reaction equation
CC1C=CC(S(O[CH2:12][C@H:13]([OH:29])[CH2:14][CH2:15][N:16]2[C:21](=[O:22])[CH:20]=[N:19][C:18]3[CH:23]=[CH:24][C:25]([O:27][CH3:28])=[N:26][C:17]2=3)(=O)=O)=CC=1.C(=O)([O-])[O-].[K+].[K+]>CO>[CH3:28][O:27][C:25]1[CH:24]=[CH:23][C:18]2[N:19]=[CH:20][C:21](=[O:22])[N:16]([CH2:15][CH2:14][C@@H:13]3[CH2:12][O:29]3)[C:17]=2[N:26]=1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 86724995(2R)-2-Hydroxy-4-(6-methoxy-3-oxopyrido[2,3-b]pyrazin-4(3H)-yl)butyl 4-methylbenzensulfonate

Product 1

HCID 867249966-Methoxy-4-{2-[(2R)-oxiran-2-yl]ethyl}pyrido[2,3-b]pyrazin-3(4H)-one

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In methanol (250 ml) was dissolved (2R)-2-hydroxy-4-(6-methoxy-3-oxopyrido[2,3-b]pyrazin-4(3H)-yl)butyl 4-methylbenzensulfonate (4.30 g, 10.25 mmol), potassium carbonate (1.70 g, 12.30 mmol) was added thereto at room temperature and the mixture was stirred for 4 hours. The reaction solution was concentrated under reduced pressure and the residue was diluted with chloroform and washed with water. After drying the resultant over anhydrous sodium sulfate, the solvent was removed under reduced pressure and the obtained residue was purified by silica gel column chromatography (chloroform/methanol) to yield 2.62 g (quantitative) of the title compound in the form of a yellowish solid.

Workup

  1. additionwas added
  2. concentrationThe reaction solution was concentrated under reduced pressure
  3. additionthe residue was diluted with chloroform
  4. washwashed with water
  5. dry with materialAfter drying the resultant over anhydrous sodium sulfate
  6. customthe solvent was removed under reduced pressure
  7. customthe obtained residue was purified by silica gel column chromatography (chloroform/methanol)

Sources & evidence

ORD record
ord-3332704ccac542afbf11c8b374062ae0
Source dataset
uspto-grants-2015_02
Patent number
US08952010B2

Reaction notes

Loading…