Triethylamine → HCID 67148094, compound

HRID 2426272Notes

Reaction equation

HRID 2426272 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-310dafc019c1464499564625d5fd6549
Source dataset
uspto-grants-2011_06
Patent number
US07968553B2

Reaction notes

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