Ethyl Acetoacetate → HCID 796646, compound

HRID 1604608Notes

Reaction equation

HRID 1604608 reaction equation
[NH2:1][C:2]1[C:7]([O:8]CC2C=CC=CC=2)=[CH:6][CH:5]=[CH:4][N:3]=1.[C:16](OCC)(=[O:21])[CH2:17][C:18]([CH3:20])=O.[OH-].[Na+]>>[OH:8][C:7]1[C:2]2=[N:1][C:18]([CH3:20])=[CH:17][C:16](=[O:21])[N:3]2[CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 3

HCID 8868Ethyl AcetoacetateHCID 14798Sodium HydroxideHCID 903342-Amino-3-benzyloxypyridine

Product 1

HCID 796646HCID 796646, compoundYield 20%

Conditions

Temperature
100 °C

Procedure

To a suspension of 2-amino-3-benzyloxypyridine (5.01 g) in polyphosphoricacid (40 ml) was dropwise added ethyl acetoacetate (6.51 g) at 60° C., and the mixture was warmed at 100° C. for 3 hours. The mixture was poured into ice water, neutralized with sodium hydroxide and extracted with chloroform. The extract was washed with water, dried over magnesium sulfate and concentrated in vacuo. The residue was purified by flash chromatography (methanol-chloroform) to give 9-hydroxy-2-methyl-4H-pyrido[1,2-a]pyrimidin-4-one (880 mg).

Workup

  1. customat 60° C.
  2. extractionextracted with chloroform
  3. washThe extract was washed with water
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash chromatography (methanol-chloroform)

Sources & evidence

ORD record
ord-7de1f5de5a694c978c35a5660cad9edf
Source dataset
uspto-grants-1999_11
Patent number
US05994368

Reaction notes

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