Piperidine → HCID 57677323, compound

HRID 492724Notes

Reaction equation

HRID 492724 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([O:8][C:9]2[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][C:10]=2[F:18])[N:5]=[CH:4][N:3]=1.C(N(CC)CC)C.Cl[C:27](OC1C=CC=CC=1)=[O:28].[NH:36]1[CH2:41][CH2:40][CH2:39][CH2:38][CH2:37]1>O1CCCC1>[F:18][C:10]1[CH:11]=[C:12]([N+:15]([O-:17])=[O:16])[CH:13]=[CH:14][C:9]=1[O:8][C:6]1[N:5]=[CH:4][N:3]=[C:2]([NH:1][C:27]([N:36]2[CH2:41][CH2:40][CH2:39][CH2:38][CH2:37]2)=[O:28])[CH:7]=1

Participants

6

Reactant 4

HCID 8082PiperidineHCID 8471TriethylamineHCID 15891Phenyl chloroformateHCID 231530124-Amino-6-(2-fluoro-4-nitrophenoxy)pyrimidine

Product 1

HCID 57677323HCID 57677323, compoundYield 63.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-Amino-6-(2-fluoro-4-nitrophenoxy)pyrimidine (300 mg) was dissolved in tetrahydrofuran (5 ml) under a nitrogen atmosphere, and then triethylamine (0.335 ml) and phenyl chloroformate (0.301 ml) were added dropwise thereto while cooling in an ice bath, followed by stirring at room temperature for 45 min. To the reaction mixture was added piperidine (0.446 ml), followed by stirring at room temperature for 45 min. The reaction mixture was partitioned between ethyl acetate and a saturated aqueous solution of ammonium chloride. The organic layer was washed with a saturated aqueous solution of ammonium chloride, a 1 N aqueous solution of sodium hydroxide, water and brine in this order, and dried over anhydrous sodium sulfate. The solvent was evaporated under a reduced pressure to give a residue, which was then purified by silica gel column chromatography (eluent; hexane:ethyl acetate=3:2). Fractions containing the target compound was concentrated under a reduced pressure, and dried in vacuum to provide the titled compound (275.4 mg, 63.5%) as a pale yellow oil.

Workup

  1. temperaturewhile cooling in an ice bath
  2. stirringby stirring at room temperature for 45 min
  3. customThe reaction mixture was partitioned between ethyl acetate
  4. washThe organic layer was washed with a saturated aqueous solution of ammonium chloride
  5. dry with materiala 1 N aqueous solution of sodium hydroxide, water and brine in this order, and dried over anhydrous sodium sulfate
  6. customThe solvent was evaporated under a reduced pressure
  7. customto give a residue, which
  8. customwas then purified by silica gel column chromatography (eluent; hexane:ethyl acetate=3:2)
  9. additionFractions containing the target compound
  10. concentrationwas concentrated under a reduced pressure
  11. customdried in vacuum

Sources & evidence

ORD record
ord-db40d555b20e4977b831d10b1626d74e
Source dataset
uspto-grants-2009_05
Patent number
US07531532B2

Reaction notes

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