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Cesium carbonate → tert-butyl 7-[(5-cyclopropylpyrazin-2-yl)oxy]-6-oxohexahydropyrrolo[1,2-a]pyrazine-2(1H)-carboxylate

HRID 240456
Notes
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Reaction equation

HRID 240456 reaction equation
[OH:1][CH:2]1[C:17](=[O:18])[N:5]2[CH2:6][CH2:7][N:8]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:9][CH:4]2[CH2:3]1.C(=O)([O-])[O-].[Cs+].[Cs+].Br[C:26]1[CH:31]=[N:30][C:29]([CH:32]2[CH2:34][CH2:33]2)=[CH:28][N:27]=1>C(#N)C>[CH:32]1([C:29]2[N:30]=[CH:31][C:26]([O:1][CH:2]3[C:17](=[O:18])[N:5]4[CH2:6][CH2:7][N:8]([C:10]([O:12][C:13]([CH3:15])([CH3:14])[CH3:16])=[O:11])[CH2:9][CH:4]4[CH2:3]3)=[N:27][CH:28]=2)[CH2:34][CH2:33]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 457876352-Bromo-5-cyclopropylpyrazineHCID 86680464tert-butyl 7-hydroxy-6-oxohexahydropyrrolo[1,2-a]pyrazine-2(1H)-carboxylate

Product 1

HCID 86680465tert-butyl 7-[(5-cyclopropylpyrazin-2-yl)oxy]-6-oxohexahydropyrrolo[1,2-a]pyrazine-2(1H)-carboxylateYield 63.1%

Reagents, catalysts & solvents 1

HCID 6342
Acetonitrile
Solvent

Conditions

Temperature
50 °C

Procedure

To a solution of the product from Example 207B (89 mg, 0.347 mmol) in anhydrous acetonitrile (3.5 mL) was added cesium carbonate (226 mg, 0.695 mmol) and 2-bromo-5-cyclopropylpyrazine (104 mg, 0.521 mmol). The resulting mixture was stirred under N2 at 50° C. for 48 hours. The mixture was allowed to cool to room temperature and partitioned between water and ethyl acetate (3×). The combined organic layers were dried over Na2SO4. The drying agent was removed by filtration, and the filtrate was concentrated in vacuo. The crude product was purified by column chromatography on silica gel using a solvent gradient of 0-10% CH3OH in CH2Cl2 to give the title compound (82 mg, 63%).

Workup

  1. temperatureto cool to room temperature
  2. custompartitioned between water and ethyl acetate (3×)
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. customThe drying agent was removed by filtration
  5. concentrationthe filtrate was concentrated in vacuo
  6. customThe crude product was purified by column chromatography on silica gel using a solvent gradient of 0-10% CH3OH in CH2Cl2

Sources & evidence

ORD record
ord-682614dd95f94014bde68f6f8b336487
Source dataset
uspto-grants-2014_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08648074B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes