Dimethylformamide → HCID 11290761, compound

HRID 1666547Notes

Reaction equation

C(=O)([O-])[O-].[K+].[K+].CN(C=O)C.[CH:12]1([N:17]2[CH2:22][CH2:21][CH:20]([O:23][C:24]3[N:29]=[CH:28][C:27](Br)=[CH:26][N:25]=3)[CH2:19][CH2:18]2)[CH2:16][CH2:15][CH2:14][CH2:13]1.[NH:31]1[CH:36]=[CH:35][CH:34]=[CH:33][C:32]1=[O:37]>[Cu](I)I.O>[CH:12]1([N:17]2[CH2:22][CH2:21][CH:20]([O:23][C:24]3[N:29]=[CH:28][C:27]([N:31]4[CH:36]=[CH:35][CH:34]=[CH:33][C:32]4=[O:37])=[CH:26][N:25]=3)[CH2:19][CH2:18]2)[CH2:16][CH2:15][CH2:14][CH2:13]1

Participants

Conditions

Temperature: 150 °C

Procedure

Potassium carbonate (40 mg) and copper iodide (40 mg) were added to a DMF solution (5 ml) of 2-(1-cyclopentylpiperidin-4-yloxy)-5-bromopyrimidine (130 mg) and 1H-pyridin-2-one (19 mg), and stirred at 150° C. for 3 hours. The reaction mixture was cooled to room temperature, water was added to it and extracted with ethyl acetate. The organic layer was washed with saturated saline solution, dried with anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified through silica gel column chromatography (C-300, chloroform:methanol=9:1) to obtain the entitled compound (11 mg).

Workup

temperatureThe reaction mixture was cooled to room temperature
extractionextracted with ethyl acetate
washThe organic layer was washed with saturated saline solution
dry with materialdried with anhydrous magnesium sulfate
concentrationconcentrated under reduced pressure
customThe residue was purified through silica gel column chromatography (C-300, chloroform:methanol=9:1)

Sources & evidence

ORD record: ord-59a39a239193475da97793799b8f65df
Source dataset: uspto-grants-2011_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08044070B2

Reaction notes

Loading…