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Water → 4-{2-[(4S)-2,2-Dimethyl-1,3-dioxolan-4yl]ethyl}-6-methoxypyrido[2,3-b]pyrazin-3(4H)-one

HRID 1847063
Notes
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Reaction equation

HRID 1847063 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[N:11]=[CH:10][C:9](=[O:12])[NH:8][C:7]=2[N:13]=1.I[CH2:15][CH2:16][C@H:17]1[CH2:21][O:20][C:19]([CH3:23])([CH3:22])[O:18]1.C(=O)([O-])[O-].[Cs+].[Cs+].O>CN(C)C=O>[CH3:22][C:19]1([CH3:23])[O:18][C@@H:17]([CH2:16][CH2:15][N:8]2[C:9](=[O:12])[CH:10]=[N:11][C:6]3[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[N:13][C:7]2=3)[CH2:21][O:20]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 11076039(4S)-4-(2-iodoethyl)-2,2-dimethyl-1,3-dioxolaneHCID 667398036-Methoxypyrido[2,3-B]pyrazin-3(4H)-one

Product 1

HCID 867249884-{2-[(4S)-2,2-Dimethyl-1,3-dioxolan-4yl]ethyl}-6-methoxypyrido[2,3-b]pyrazin-3(4H)-oneYield 90.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

In N,N-dimethylformamide (400 ml) were dissolved 6-methoxypyrido[2,3-b]pyrazin-3(4H)-one (14.53 g, 82.00 mmol) and (4S)-4-(2-iodoethyl)-2,2-dimethyl-1,3-dioxolane (23.10 g, 90.20 mmol). Cesium carbonate (34.7 g, 1.06.6 mmol) was added to the solution and the mixture was stirred at 50° C. for 11 hours. After cooling in the air, water was added to the reaction solution and the mixture was extracted with ethyl acetate. The extract was washed with saturated sodium chloride solution, dried over anhydrous sodium sulfate and the solvent was removed under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate) to yield 22.58 g (90%) of the title compound in the form of a yellow orange oily product.

Workup

  1. additionwas added to the reaction solution
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed with saturated sodium chloride solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. customthe solvent was removed under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-c282702056b4447d822addf48c0fef1f
Source dataset
uspto-grants-2015_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08952010B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes