Potassium Carbonate → 6-(Methyloxy)-4-{2-[(2S)-2-oxiranyl]ethyl}pyrido[2,3-b]pyrazin-3(4H)-one

HRID 1847065Notes

Reaction equation

HRID 1847065 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 86724989(2S)-2-hydroxy-4-(6-methoxy-3-oxopyrido[2,3-b]pyrazin-4(3H)-yl)butyl 4-methylbenzenesulfonate

Product 1

HCID 866497106-(Methyloxy)-4-{2-[(2S)-2-oxiranyl]ethyl}pyrido[2,3-b]pyrazin-3(4H)-oneYield 62.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In methanol (15 ml) was dissolved (2S)-2-hydroxy-4-(6-methoxy-3-oxopyrido[2,3-b]pyrazin-4(3H)-yl)butyl 4-methylbenzenesulfonate (227 mg, 0.540 mmol), and potassium carbonate (90 mg, 0.648 mmol) was then added to the solution at room temperature. The obtained mixture was stirred for 17 hours. Thereafter, the solvent was removed from the reaction solution under reduced pressure. The obtained residue was purified by silica gel column chromatography (chloroform/methanol) to yield 83 mg (62%) of the above-captioned compound in the form of a yellow solid.

Workup

  1. additionwas then added to the solution at room temperature
  2. customThereafter, the solvent was removed from the reaction solution under reduced pressure
  3. customThe obtained residue was purified by silica gel column chromatography (chloroform/methanol)

Sources & evidence

ORD record
ord-8206dbe5f6d349a6af6c6752a8445cdc
Source dataset
uspto-grants-2015_02
Patent number
US08952010B2

Reaction notes

Loading…