Ethyl Acetate → 2-tert-Butoxy-4-[2-[4-(2-fluorophenoxymethyl)piperidino]ethyl]pyrimidine

HRID 914873Notes

Reaction equation

HRID 914873 reaction equation
[C:1]([O:5][C:6]1[N:11]=[C:10]([CH:12]=[CH2:13])[CH:9]=[CH:8][N:7]=1)([CH3:4])([CH3:3])[CH3:2].Cl.[F:15][C:16]1[CH:29]=[CH:28][CH:27]=[CH:26][C:17]=1[O:18][CH2:19][CH:20]1[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]1.C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>C(O)C>[C:1]([O:5][C:6]1[N:11]=[C:10]([CH2:12][CH2:13][N:23]2[CH2:22][CH2:21][CH:20]([CH2:19][O:18][C:17]3[CH:26]=[CH:27][CH:28]=[CH:29][C:16]=3[F:15])[CH2:25][CH2:24]2)[CH:9]=[CH:8][N:7]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 171780504-((2-Fluorophenoxy)methyl)piperidine hydrochlorideHCID 222481652-Tert-butoxy-4-vinylpyrimidine

Product 1

HCID 222479962-tert-Butoxy-4-[2-[4-(2-fluorophenoxymethyl)piperidino]ethyl]pyrimidineYield 93%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

After dissolving 221 mg of 2-tert-butoxy-4-vinylpyrimidine and 200 mg of 4-(2-fluorophenoxymethyl)piperidine hydrochloride in 5 ml of ethanol, 123 mg of anhydrous potassium carbonate was added and the mixture was heated to reflux for 50 minutes. Ethyl acetate was added to the reaction mixture, the insoluble portion was filtered off, and the filtrate was concentrated under reduced pressure. The residue was purified by NH silica gel column chromatography (solvent: n-hexane/ethyl acetate) to obtain the title compound (293 mg, 93% yield).

Workup

  1. additionwas added
  2. temperaturethe mixture was heated
  3. temperatureto reflux for 50 minutes
  4. filtrationthe insoluble portion was filtered off
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customThe residue was purified by NH silica gel column chromatography (solvent: n-hexane/ethyl acetate)

Sources & evidence

ORD record
ord-1e31f78493a24fd4ac3196e04a19d8ae
Source dataset
uspto-grants-2007_09
Patent number
US07265108B2

Reaction notes

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