Piperidine → 2,4-Dichloro-6-(piperidin-1-yl)pyrimidine

HRID 2375470Notes

Reaction equation

HRID 2375470 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[CH:5]=[C:4]([Cl:9])[N:3]=1.[NH:10]1[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1.C(N(CC)C(C)C)(C)C>O1CCCC1>[Cl:1][C:2]1[N:3]=[C:4]([Cl:9])[CH:5]=[C:6]([N:10]2[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]2)[N:7]=1

Participants

5

Reactant 3

HCID 8082PiperidineHCID 773782,4,6-TrichloropyrimidineHCID 81531Diisopropylethylamine

Product 1

HCID 211012992,4-Dichloro-6-(piperidin-1-yl)pyrimidineYield 59%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 2,4,6-trichloropyrimidine (5.0 g, 27 mmol) and piperidine (2.3 g, 27 mmol) in tetrahydrofuran (50 mL) and N,N-diisopropylethylamine (3.5 g, 27 mmol) was stirred at room temperature for 24 hours. The solvent was removed and the crude material was purified by flash chromatography on silica gel. The column was eluted with a gradient of hexane to yield ethyl acetate/hexane (1:4). The eluent was removed, giving 2,4-dichloro-6-(1-piperidinyl)pyrimidine (3.67 g, 15.8 mmol, 59%, Rf=0.58 in ethyl acetate/hexane, 1:4).

Workup

  1. customThe solvent was removed
  2. customthe crude material was purified by flash chromatography on silica gel
  3. washThe column was eluted with a gradient of hexane
  4. customto yield ethyl acetate/hexane (1:4)
  5. customThe eluent was removed

Sources & evidence

ORD record
ord-2aa7727b12414d3a948b29e0d0269ac4
Source dataset
uspto-grants-2008_12
Patent number
US07465750B2

Reaction notes

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