Potassium Carbonate → HCID 68568581, compound

HRID 1811554Notes

Reaction equation

HRID 1811554 reaction equation
[CH:1]([O:4][C:5]([N:7]1[CH2:12][CH2:11][CH:10]([O:13][C:14]2[C:19]([O:20][CH3:21])=[C:18](Cl)[N:17]=[CH:16][N:15]=2)[CH2:9][CH2:8]1)=[O:6])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].[Br:29][C:30]1[CH:35]=[CH:34][C:33]([OH:36])=[C:32]([F:37])[CH:31]=1>CC(N(C)C)=O>[CH:1]([O:4][C:5]([N:7]1[CH2:12][CH2:11][CH:10]([O:13][C:14]2[C:19]([O:20][CH3:21])=[C:18]([O:36][C:33]3[CH:34]=[CH:35][C:30]([Br:29])=[CH:31][C:32]=3[F:37])[N:17]=[CH:16][N:15]=2)[CH2:9][CH2:8]1)=[O:6])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 27249814-Bromo-2-fluorophenolHCID 51050526Isopropyl 4-[(6-chloro-5-methoxypyrimidin-4-yl)oxy]piperidine-1-carboxylate

Product 1

HCID 68568581HCID 68568581, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
160 °C

Procedure

A mixture of 4-(6-chloro-5-methoxy-pyrimidin-4-yloxy)-piperidine-1-carboxylic acid isopropyl ester (2.19 g, 6.7 mmol), potassium carbonate (1.84 g, 13.3 mmol), and 4-bromo-2-fluorophenol (1.65 g, 8.65 mmol) in 32 ml DMA was heated at 160° C. for 5 hours. The mixture was extracted with AcOEt and brine. Organic phase was dried over MgSO4, filtered and concentrated. The residue was purified by HPLC to give 4-[6-(4-bromo-2-fluoro-phenoxy)-5-methoxy-pyrimidin-4-yloxy]-piperidine-1-carboxylic acid isopropyl ester as an oil (1.12 g, 35%). Exact mass calculated for C20H23BrFN3O5 483.08. found 484.4 (MH+).

Workup

  1. extractionThe mixture was extracted with AcOEt and brine
  2. dry with materialOrganic phase was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by HPLC

Sources & evidence

ORD record
ord-8ba98f2c408e4081828da5c158e17ed9
Source dataset
uspto-grants-2013_01
Patent number
US08362248B2

Reaction notes

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