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

HRID 606219Notes

Reaction equation

HRID 606219 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-2db74d89b0974e5d91c9442f241f260d
Source dataset
uspto-grants-2011_03
Patent number
US07915274B2

Reaction notes

Loading…