Potassium Carbonate → 6-Acetoxy-5-oxo-1-(2-oxo-2-piperidin-1-yl-ethyl)-1,5-dihydro-imidazo[1,2-a]pyrimidine-7-carboxylic acid methyl ester

HRID 1971814Notes

Reaction equation

HRID 1971814 reaction equation
[CH3:1][O:2][C:3]([C:5]1[N:6]=[C:7]2[NH:18][CH:17]=[CH:16][N:8]2[C:9](=[O:15])[C:10]=1[O:11][C:12](=[O:14])[CH3:13])=[O:4].Cl[CH2:20][C:21]([N:23]1[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1)=[O:22].C([O-])([O-])=O.[K+].[K+]>C(#N)C>[CH3:1][O:2][C:3]([C:5]1[N:6]=[C:7]2[N:18]([CH2:20][C:21](=[O:22])[N:23]3[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]3)[CH:17]=[CH:16][N:8]2[C:9](=[O:15])[C:10]=1[O:11][C:12](=[O:14])[CH3:13])=[O:4]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 2223122-Chloro-1-piperidine-1-yl-ethanoneHCID 178499055HCID 178499055, compound

Product 1

HCID 581269386-Acetoxy-5-oxo-1-(2-oxo-2-piperidin-1-yl-ethyl)-1,5-dihydro-imidazo[1,2-a]pyrimidine-7-carboxylic acid methyl esterYield 66.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of compound 6-acetoxy-5-oxo-1,5-dihydro-imidazo[1,2-a]pyrimidine-7-carboxylic acid methyl ester (PCT/AU2007/001980) (2.0 g, 7.96 mmol) in anhydrous acetonitrile (20 ml) was added compound 2-chloro-1-piperidin-1-yl-ethanone (2.0 g, 12.42 mmol), K2CO3 (1.7 g, 12.32 mmol), KI (133 mg, 0.8 mmol) successively. The mixture was heated at refluxed for 3 hours. After cooling to the room temperature, the mixture was filtered and the filtrate was concentrated under reduced pressure. The resulting residue was recrystallized from ethyl acetate to give titled compound (2.0 g, yield 66.7%).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat refluxed for 3 hours
  3. filtrationthe mixture was filtered
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe resulting residue was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-585e35198dad4498bd92c9826ca2fca8
Source dataset
uspto-grants-2013_04
Patent number
US08431581B2

Reaction notes

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