Potassium Carbonate → 1-(2-Cyclopropyl-ethyl)-4-methoxy-2-oxo-1,2-dihydro-pyridine-3-carbonitrile

HRID 2401671Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:8]=[CH:7][NH:6][C:5](=[O:9])[C:4]=1[C:10]#[N:11].[CH:12]1([CH2:15][CH2:16]OS(C)(=O)=O)[CH2:14][CH2:13]1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH:12]1([CH2:15][CH2:16][N:6]2[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[C:4]([C:10]#[N:11])[C:5]2=[O:9])[CH2:14][CH2:13]1

Participants

Conditions

Temperature: 105 °C

Procedure

To a solution of 4-methoxy-2-oxo-1,2-dihydro-pyridine-3-carbonitrile (19.81 g, 131.98 mmol) in acetonitrile (520 ml) were added intermediate 1 (34.36 g, 171.57 mmol) and potassium carbonate (56.73 g, 410.3 mmol) and the mixture was heated at 105° C. for 12 hours. The mixture was cooled to room temperature and the solid was filtered off The filtrate was evaporated till dryness. The crude product was purified by column chromatography (silica gel; DCM to DCM/EtOAc up to 20% as eluent). The desired fractions were collected and evaporated in vacuo to yield intermediate 3 (13.18 g, 46%).

Workup

temperatureThe mixture was cooled to room temperature
filtrationthe solid was filtered off The filtrate
customwas evaporated till dryness
customThe crude product was purified by column chromatography (silica gel; DCM to DCM/EtOAc up to 20% as eluent)
customThe desired fractions were collected
customevaporated in vacuo

Sources & evidence

ORD record: ord-c7078a9c8b654e1a8bd953f35e2d05be
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08796311B2

Reaction notes

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