Cesium carbonate → Ethyl 5-(cyclopropylmethyl)-4-oxo-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazine-2-carboxylate

HRID 1842471Notes

Reaction equation

[CH:1]1([CH2:4]Br)[CH2:3][CH2:2]1.[O:6]=[C:7]1[NH:12][CH2:11][CH2:10][N:9]2[N:13]=[C:14]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH:15]=[C:8]12.C(=O)([O-])[O-].[Cs+].[Cs+]>C(#N)C>[CH:1]1([CH2:4][N:12]2[CH2:11][CH2:10][N:9]3[N:13]=[C:14]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH:15]=[C:8]3[C:7]2=[O:6])[CH2:3][CH2:2]1

Participants

Conditions

Temperature: 70 °C

Procedure

To a solution of cyclopropylmethyl bromide (0.101 g, 0.75 mmol) and ethyl 4-oxo-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazine-2-carboxylate (31.4 mg, 0.150 mmol) in acetonitrile (2 mL) was added cesium carbonate (147 mg, 0.45 mmol). The reaction mixture was heated overnight at 70° C. Upon cooling to room temperature, the insolubles were removed by filtration and the solvent evaporated to dryness to afford crude Intermediate 33.

Workup

temperatureUpon cooling to room temperature
customthe insolubles were removed by filtration
customthe solvent evaporated to dryness

Sources & evidence

ORD record: ord-df742b2d93744e508a5331f72e5a87af
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08946223B2

Reaction notes

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