2,4-Dichloro-6-methylpyrimidine → HCID 15512220, compound

HRID 635210Notes

Reaction equation

HRID 635210 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[CH:5]=[C:4]([CH3:9])[N:3]=1.Cl.[C:11]1([C:17]2[CH2:18][CH2:19][NH:20][CH2:21][CH:22]=2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(N(C(C)C)CC)(C)C.C(=O)([O-])O.[Na+]>C(O)C>[C:11]1([C:17]2[CH2:22][CH2:21][N:20]([C:6]3[CH:5]=[C:4]([CH3:9])[N:3]=[C:2]([Cl:1])[N:7]=3)[CH2:19][CH:18]=2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

6

Reactant 4

HCID 794712,4-Dichloro-6-methylpyrimidineHCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 27238604-Phenyl-1,2,3,6-tetrahydropyridine hydrochloride

Product 1

HCID 15512220HCID 15512220, compoundYield 67.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In 4 ml of ethanol was dissolved 415 mg of 2,4-dichloro-6-methylpyrimidine, and the solution was cooled with ice-water. To the solution were added 503 mg of 4-phenyl-1,2,3,6-tetrahydropyridine hydrochloride and 664 mg of diisopropylethylamine, followed by stirring overnight under cooling with ice. The reaction solution was poured into a saturated aqueous solution of sodium hydrogencarbonate and extracted with ethyl acetate. The extract was washed with a saturated aqueous sodium chloride solution and dried over anhydrous sodium sulfate. The desiccant was removed by filtration, the filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (developing solvent: hexane/ethyl acetate=10/1 to 3/1) to give 491 mg of 4-(4-phenyl-1,2,3,6-tetrahydropyridin-1-yl)-2-chloro-6-methylpyrimidine as crystals.

Workup

  1. temperatureunder cooling with ice
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with a saturated aqueous sodium chloride solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe desiccant was removed by filtration
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. customthe residue was purified by silica gel column chromatography (developing solvent: hexane/ethyl acetate=10/1 to 3/1)

Sources & evidence

ORD record
ord-b7143ff13d6141cfb09569a48565fd3a
Source dataset
uspto-grants-2001_02
Patent number
US06187781B1

Reaction notes

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