2,4-Dichloropyrimidine → HCID 75539526, compound

HRID 1019650Notes

Reaction equation

HRID 1019650 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[CH:5]=[CH:4][N:3]=1.[NH:9]1[CH2:14][CH2:13][CH2:12][CH:11]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH2:10]1>CCO>[Cl:1][C:2]1[N:7]=[C:6]([N:9]2[CH2:14][CH2:13][CH2:12][CH:11]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH2:10]2)[CH:5]=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 775312,4-DichloropyrimidineHCID 98969Ethyl nipecotate

Product 1

HCID 75539526HCID 75539526, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a solution of 2,4-dichloropyrimidine (Alfa Aesar, 10 g, 65.8 mmol) and TEA (Sigma-Aldrich, 9.15 mL, 65.8 mmol) in EtOH (68.5 mL) at 0° C. was added ethyl piperidine-3-carboxylate (Sigma-Aldrich, 10.64 mL, 65.8 mmol) in EtOH (13.70 mL). The reaction was then allowed to warm to room temperature while stirring. After 1 hour, the reaction was concentrated and the residue was purified by chromatography through a 340 g silica gel column, eluting with 10% to 80% EtOAc/hexanes, to provide ethyl 1-(2-chloropyrimidin-4-yl)piperidine-3-carboxylate as a colorless oil in 80% yield. 1H NMR (300 MHz, CDCl3) δ ppm 0.94 (t, J=6.94 Hz, 3H) 1.26 (d, J=9.35 Hz, 1H) 1.38-1.62 (m, 2H) 1.66-1.85 (m, 1H) 2.26 (m, 1H) 2.90-3.20 (m, 2H) 3.64 (m, 1H) 3.69-4.09 (m, 3H) 6.23 (d, J=5.85 Hz, 1H) 7.68 (d, J=5.99 Hz, 1H); ESI-MS M+H 270.0.

Workup

  1. concentrationthe reaction was concentrated
  2. customthe residue was purified by chromatography through a 340 g silica gel column
  3. washeluting with 10% to 80% EtOAc/hexanes

Sources & evidence

ORD record
ord-68f53f4507e84859ad8de178b6d43a69
Source dataset
uspto-grants-2014_05
Patent number
US08716281B2

Reaction notes

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