Piperidine → HCID 66955386, compound

HRID 1399725Notes

Reaction equation

HRID 1399725 reaction equation
[CH3:1][C:2]1[NH:7][C:6](=O)[N:5]=[C:4]([C:9]2[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][CH:10]=2)[C:3]=1[C:16]([O:18][CH2:19][CH3:20])=[O:17].C1CN([P+](Br)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.C(N(CC)CC)C.[NH:52]1[CH2:57][CH2:56][CH2:55][CH2:54][CH2:53]1>O1CCOCC1.C(OCC)(=O)C>[CH3:1][C:2]1[C:3]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[C:4]([C:9]2[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][CH:10]=2)[N:5]=[C:6]([N:52]2[CH2:57][CH2:56][CH2:55][CH2:54][CH2:53]2)[N:7]=1

Participants

7

Reactant 4

HCID 8082PiperidineHCID 8471TriethylamineHCID 2733179PyBroPHCID 66955389HCID 66955389, compound

Product 1

HCID 66955386HCID 66955386, compound

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

To a stirred solution of ethyl 6-methyl-2-oxo-4-p-tolyl-1,2-dihydropyrimidine-5-carboxylate (2 g; 7,34 mmol) in dioxane (35 mL) were added PyBrOP (3,77 g; 8,08 mmol), triethyl amine (2,06 mL; 14,69 mmol) and piperidine (0,945 mL; 9,55 mmol) and the mixture was stirred at room temperature for 4 days. The reaction mixture was diluted with ethyl acetate and washed with a saturated solution of ammonium chloride and brine, dried over sodium sulphate, filtered and concentrated under reduced pressure. Purification by flash-chromatography on silica gel using a gradient of ethyl acetate (2-20%) in heptane furnished 2 g (80%) of the title as a yellow oil.

Workup

  1. washwashed with a saturated solution of ammonium chloride and brine
  2. dry with materialdried over sodium sulphate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customPurification by flash-chromatography on silica gel using a gradient of ethyl acetate (2-20%) in heptane
  6. customfurnished 2 g (80%) of the title as a yellow oil

Sources & evidence

ORD record
ord-110bf5f969074b1290666e08e3b0ec5d
Source dataset
uspto-grants-2014_12
Patent number
US08906906B2

Reaction notes

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