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

HRID 1352886Notes

Reaction equation

HRID 1352886 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-5994cf2c81a44c3aa442f51cc0b35534
Source dataset
uspto-grants-2007_05
Patent number
US07220775B2

Reaction notes

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