3,4,5-Trimethoxyaniline → HCID 67479322, compound

HRID 1019657Notes

Reaction equation

HRID 1019657 reaction equation
Cl[C:2]1[N:7]=[C:6](Cl)[C:5]([CH3:9])=[CH:4][N:3]=1.[NH:10]1[CH2:15][CH2:14][CH2:13][CH:12]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH2:11]1.[CH3:21][O:22][C:23]1[CH:24]=[C:25]([CH:27]=[C:28]([O:32][CH3:33])[C:29]=1[O:30][CH3:31])[NH2:26]>CCO>[CH3:9][C:5]1[C:6]([N:10]2[CH2:15][CH2:14][CH2:13][CH:12]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH2:11]2)=[N:7][C:2]([NH:26][C:25]2[CH:27]=[C:28]([O:32][CH3:33])[C:29]([O:30][CH3:31])=[C:23]([O:22][CH3:21])[CH:24]=2)=[N:3][CH:4]=1

Participants

5

Reactant 3

HCID 322853,4,5-TrimethoxyanilineHCID 74508Pyrimidine, 2,4-dichloro-5-methyl-HCID 98969Ethyl nipecotate

Product 1

HCID 67479322HCID 67479322, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a solution of 2,4-dichloro-5-methylpyrimidine (Sigma-Aldrich, 1 g, 6.13 mmol) and TEA (0.855 mL, 6.13 mmol) in EtOH (6.39 mL) was added ethyl piperidine-3-carboxylate (0.993 mL, 6.13 mmol) in EtOH (1.278 mL). The reaction was then allowed to stir at room temperature. After 4 hours, 3,4,5-trimethoxyaniline (1.124 g, 6.13 mmol) was added and the reaction was heated in the microwave to 150° C. for 30 minutes. The reaction was then cooled to room temperature and concentrated to dryness. The residue was adsorbed onto a plug of silica gel and purified by chromatography through a 100 g silica gel column, eluting with 10% to 100% EtOAc in hexanes to provide 8.1. ESI-MS M+H 430.8.

Workup

  1. temperaturethe reaction was heated in the microwave to 150° C. for 30 minutes
  2. temperatureThe reaction was then cooled to room temperature
  3. concentrationconcentrated to dryness
  4. custompurified by chromatography through a 100 g silica gel column
  5. washeluting with 10% to 100% EtOAc in hexanes
  6. customto provide 8.1

Sources & evidence

ORD record
ord-87aa74a6b70141d29955f7f03361df11
Source dataset
uspto-grants-2014_05
Patent number
US08716281B2

Reaction notes

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