Potassium Carbonate → 6-Acetoxy-1-[2-(3,5-dimethyl-piperidin-1-yl)-2-oxo-ethyl]-5-oxo-1,5-dihydro-imidazo[1,2-a]pyrimidine-7-carboxylic acid methyl ester

HRID 1971854Notes

Reaction equation

HRID 1971854 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].C([O-])([O-])=O.[K+].[K+].C1OCCOCCOCCOCCOCCOC1.Br[CH2:44][C:45]([N:47]1[CH2:52][CH:51]([CH3:53])[CH2:50][CH:49]([CH3:54])[CH2:48]1)=[O:46]>C(#N)C>[CH3:1][O:2][C:3]([C:5]1[N:6]=[C:7]2[N:18]([CH2:44][C:45]([N:47]3[CH2:52][CH:51]([CH3:53])[CH2:50][CH:49]([CH3:54])[CH2:48]3)=[O:46])[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

6

Reactant 4

HCID 11430Potassium CarbonateHCID 2855718-Crown-6HCID 532157732-Bromo-1-(3,5-dimethyl-piperidin-1-yl)-ethanoneHCID 178499055HCID 178499055, compound

Product 1

HCID 581269216-Acetoxy-1-[2-(3,5-dimethyl-piperidin-1-yl)-2-oxo-ethyl]-5-oxo-1,5-dihydro-imidazo[1,2-a]pyrimidine-7-carboxylic acid methyl esterYield 60.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

6-Acetoxy-5-oxo-1,5-dihydro-imidazo[1,2-a]pyrimidine-7-carboxylic acid methyl ester (3 g, 11.95 mmol) was mixed with K2CO3 (3.3 g, 23.9 mmol), 18-crown-6 ether (0.3 g) and 2-Bromo-1-(3,5-dimethyl-piperidin-1-yl)-ethanone (4.2 g, 17.93 mmol) in acetonitrile (60 ml). The resulting mixture was stirred overnight at room temperature. The solvents were removed, and the residue taken up in ethylacetate; washed with water and 1N HCl. After drying over MgSO4, the organic phase was evaporated to dryness and the residue was purified on silica gel to give 6-acetoxy-1-[2-(3,5-dimethyl-piperidin-1-yl)-2-oxo-ethyl]-5-oxo-1,5-dihydro-imidazo[1,2-a]pyrimidine-7-carboxylic acid methyl ester (2.92 g, 60.5% yield).

Workup

  1. customThe solvents were removed
  2. washwashed with water and 1N HCl
  3. dry with materialAfter drying over MgSO4
  4. customthe organic phase was evaporated to dryness
  5. customthe residue was purified on silica gel

Sources & evidence

ORD record
ord-58f0eac30c474aefa874eddc6816d4e7
Source dataset
uspto-grants-2013_04
Patent number
US08431581B2

Reaction notes

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