Benzyl Bromide → Ethyl 5-benzyl-4-oxo-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazine-2-carboxylate

HRID 1842470Notes

Reaction equation

[O:1]=[C:2]1[NH:7][CH2:6][CH2:5][N:4]2[N:8]=[C:9]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH:10]=[C:3]12.C(=O)([O-])[O-].[Cs+].[Cs+].[CH2:22](Br)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>C(#N)C>[CH2:22]([N:7]1[CH2:6][CH2:5][N:4]2[N:8]=[C:9]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH:10]=[C:3]2[C:2]1=[O:1])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

Conditions

Temperature: 70 °C

Procedure

To a solution of ethyl 4-oxo-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazine-2-carboxylate (30 mg, 0.143 mmol) in acetonitrile (1 mL) was added cesium carbonate (93.4 mg, 0.287 mmol) and benzyl bromide (25.6 μL, 0.215 mmol). The reaction mixture was stirred overnight at 70° C. Upon cooling to room temperature, the cesium carbonate was removed by filtration and the solvent evaporated under reduced pressure to afford crude Intermediate 32. LC-MS: (AA) ES+300.

Workup

temperatureUpon cooling to room temperature
customthe cesium carbonate was removed by filtration
customthe solvent evaporated under reduced pressure

Sources & evidence

ORD record: ord-b35ffe0d16d649698dfff5b984893655
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08946223B2

Reaction notes

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