Potassium Carbonate → 6-Acetoxy-1-(2-morpholin-4-yl-ethyl)-5-oxo-1,5-dihydro-imidazo[1,2-a]pyrimidine-7-carboxylic acid methyl ester

HRID 536136Notes

Reaction equation

HRID 536136 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].C1OCCOCCOCCOCCOCCOC1.C(=O)([O-])[O-].[K+].[K+].Cl.Cl[CH2:45][CH2:46][N:47]1[CH2:52][CH2:51][O:50][CH2:49][CH2:48]1>C(#N)C>[CH3:1][O:2][C:3]([C:5]1[N:6]=[C:7]2[N:18]([CH2:45][CH2:46][N:47]3[CH2:52][CH2:51][O:50][CH2:49][CH2:48]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

6

Reactant 4

HCID 11430Potassium CarbonateHCID 2855718-Crown-6HCID 77210Morpholine, 4-(2-chloroethyl)-, hydrochloride (1:1)HCID 178499055HCID 178499055, compound

Product 1

HCID 574945616-Acetoxy-1-(2-morpholin-4-yl-ethyl)-5-oxo-1,5-dihydro-imidazo[1,2-a]pyrimidine-7-carboxylic acid methyl esterYield 34.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The product from Example 18.1.1.2 (30 mg, 0.12 mmol) and 18-crown-6 (3 mg, 10% w/w) were mixed with acetonitrile (5 mL) at room temperature. To this stirred solution was added anhydrous potassium carbonate (83 mg, 0.60 mmol) and 4-(2-chloroethyl)-morpholine hydrochloride (25 mg, 0.132 mmol). The mixture was heated at reflux for 2 h and then cooled down to room temperature. The reaction was concentrated to near dryness in vacuo and ethyl acetate (15 mL) was added and the mixture washed with water (2×10 mL). The organic layer was separated, dried and concentrated in vacuo and the residue was purified by column chromatography using dichloromethane/methanol (20:1) as eluent. 6-Acetoxy-1-(2-morpholin-4-yl-ethyl)-5-oxo-1,5-dihydro-imidazo[1,2-a]pyrimidine-7-carboxylic acid methyl ester (15 mg, 34%) was obtained as a white solid.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 2 h
  3. concentrationThe reaction was concentrated
  4. additionwas added
  5. washthe mixture washed with water (2×10 mL)
  6. customThe organic layer was separated
  7. customdried
  8. concentrationconcentrated in vacuo
  9. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-546822191dc2421684acc2052103f219
Source dataset
uspto-grants-2014_10
Patent number
US08859563B2

Reaction notes

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