Potassium Carbonate → HCID 68106837, compound

HRID 2403617Notes

Reaction equation

HRID 2403617 reaction equation
[ClH:1].[NH:2]1[CH2:5][CH2:4][CH2:3]1.[Cl:6][C:7]1[N:12]=[CH:11][C:10]([C:13]2[CH:14]=[C:15]([CH:30]=[CH:31][CH:32]=2)[CH2:16][N:17]([CH3:29])[C:18](=[O:28])[CH2:19][NH:20]C(=O)OC(C)(C)C)=[CH:9][N:8]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[ClH:6].[ClH:1].[N:2]1([C:7]2[N:8]=[CH:9][C:10]([C:13]3[CH:14]=[C:15]([CH:30]=[CH:31][CH:32]=3)[CH2:16][N:17]([CH3:29])[C:18](=[O:28])[CH2:19][NH2:20])=[CH:11][N:12]=2)[CH2:5][CH2:4][CH2:3]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 12308726Azetidine hydrochlorideHCID 86667972HCID 86667972, compound

Product 1

HCID 68106837HCID 68106837, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

Azetidine hydrochloride (287 mg) was suspended in DMF (5 ml), and tert-butyl (2-{[3-(2-chloropyrimidin-5-yl)benzyl](methyl)amino}-2-oxoethyl)carbamate (300 mg) and K2CO3 (849 mg) were added thereto, followed by stirring at 80° C. overnight. The reaction mixture was concentrated under reduced pressure, and then a saturated aqueous sodium hydrogen carbonate solution was added thereto, followed by extraction with CHCl3. The organic layer was dried over Na2SO4 and the solvent was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane/EtOAc). The product was dissolved in EtOH (4 ml), and 4 M hydrogen chloride/EtOAc (2 ml) was added thereto, followed by stirring at room temperature overnight. The precipitated solid was collected by filtration to obtain N-[3-(2-azetidin-1-ylpyrimidin-5-yl)benzyl]-N-methylglycinamide dihydrochloride (295 mg).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additiona saturated aqueous sodium hydrogen carbonate solution was added
  3. extractionfollowed by extraction with CHCl3
  4. dry with materialThe organic layer was dried over Na2SO4
  5. concentrationthe solvent was concentrated under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography (hexane/EtOAc)
  7. dissolutionThe product was dissolved in EtOH (4 ml)
  8. addition4 M hydrogen chloride/EtOAc (2 ml) was added
  9. stirringby stirring at room temperature overnight
  10. filtrationThe precipitated solid was collected by filtration

Sources & evidence

ORD record
ord-c6c8b4f32c364a5486af6778a5e9296f
Source dataset
uspto-grants-2014_08
Patent number
US08802679B2

Reaction notes

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