Ethyl Bromide → 1-Ethyl-piperidine-4-carboxylic acid [6-(2-ethoxy-phenyl)-pyrimidin-4-yl]-amide

HRID 1020032Notes

Reaction equation

[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]1[N:15]=[CH:14][N:13]=[C:12]([NH:16][C:17]([CH:19]2[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]2)=[O:18])[CH:11]=1)[CH3:2].C(=O)([O-])[O-].[K+].[K+].[CH2:31](Br)[CH3:32]>CN(C=O)C>[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]1[N:15]=[CH:14][N:13]=[C:12]([NH:16][C:17]([CH:19]2[CH2:24][CH2:23][N:22]([CH2:31][CH3:32])[CH2:21][CH2:20]2)=[O:18])[CH:11]=1)[CH3:2]

Participants

Conditions

Temperature: 60 °C

Procedure

To the stirred solution of piperidine-4-carboxylic acid [6-(2-ethoxy-phenyl)-pyrimidin-4-yl]-amide (compound #1A) (0.20 g, 0.61 mmol) and potassium carbonate (0.10 g, 0.72 mmol) in DMF (3 ml) was added ethyl bromide (0.07 g, 0.05 ml, 0.61 mmol) at room temperature. The reaction mixture was heated at 60° C. for one hour. The progress of the reaction was monitored by TLC. The reaction mixture was poured onto ice water and extracted with ethyl acetate (3×100 mL). The organic layers were separated, combined, dried over sodium sulfate, filtered and concentrated under reduced pressure. The crude product was purified by trituration with diethyl ether (3 ml), filtered and dried under high vacuum to afford 1-ethyl-piperidine-4-carboxylic acid [6-(2-ethoxy-phenyl)-pyrimidin-4-yl]-amide (compound #3A) (0.093 g, 43%) as a white solid.

Workup

additionThe reaction mixture was poured onto ice water
extractionextracted with ethyl acetate (3×100 mL)
customThe organic layers were separated
dry with materialdried over sodium sulfate
filtrationfiltered
concentrationconcentrated under reduced pressure
customThe crude product was purified by trituration with diethyl ether (3 ml)
filtrationfiltered
customdried under high vacuum

Sources & evidence

ORD record: ord-1b4dc147bbcf424699f80f4120dd5614
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08716296B2

Reaction notes

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