Triethylamine → HCID 67148094, compound

HRID 2219057Notes

Reaction equation

HRID 2219057 reaction equation
[C:1]([O:9][C:10]1[C:15](=[O:16])[N:14]2[CH2:17][CH2:18][CH2:19][CH:20](Br)[C:13]2=[N:12][C:11]=1[C:22]([O:24][CH3:25])=[O:23])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C>CN(C=O)C>[C:1]([O:9][C:10]1[C:15](=[O:16])[N:14]2[CH2:17][CH2:18][CH:19]=[CH:20][C:13]2=[N:12][C:11]=1[C:22]([O:24][CH3:25])=[O:23])(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 67147765HCID 67147765, compound

Product 1

HCID 67148094HCID 67148094, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of methyl 3-(benzoyloxy)-9-bromo-4-oxo-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidine-2-carboxylate (obtained following Example 2, Step 1) in anhydrous DMF was added triethylamine (2 eq.). The mixture was stirred and heated to 100° C. for 3 h. After cooling to room temperature the mixture was partitioned between 0.1 M HCl and EtOAc. The aq. phase was again extracted with EtOAc and the combined org. phases were dried over sodium sulfate, filtered, concentrated to dryness under vacuum. The crude product so obtained was used in the subsequent step without further purification. An analytical sample of the title compound was obtained by crystallization from methanol. A pale yellow solid was obtained.

Workup

  1. temperatureAfter cooling to room temperature the mixture
  2. customwas partitioned between 0.1 M HCl and EtOAc
  3. extractionThe aq. phase was again extracted with EtOAc
  4. dry with materialphases were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated to dryness under vacuum
  7. customThe crude product so obtained
  8. customwas used in the subsequent step without further purification

Sources & evidence

ORD record
ord-2fb119abc75e47b98096244d789ce04e
Source dataset
uspto-grants-2008_08
Patent number
US07414045B2

Reaction notes

Loading…