Ethyl Acetoacetate → 2-Methyl-4H-pyrido[1,2-a]pyrimidin-4-one

HRID 1801672Notes

Reaction equation

HRID 1801672 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.[C:8](OCC)(=[O:13])[CH2:9][C:10]([CH3:12])=O>C(O)(=O)C>[CH3:12][C:10]1[N:1]=[C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][N:3]2[C:8](=[O:13])[CH:9]=1

Participants

4

Reactant 2

HCID 8868Ethyl AcetoacetateHCID 104392-Aminopyridine2×

Product 1

HCID 2780932-Methyl-4H-pyrido[1,2-a]pyrimidin-4-one

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

All the 3-bromo-2-methyl-4H-pyrido[1,2-a]pyrimidin-4-ones were prepared from commercially available 2-aminopyridine derivatives. Thus, 2-aminopyridine derivative was reacted with ethyl acetoacetate in refluxing acetic acid to give 2-methyl-4H-pyrido[1,2-a]pyrimidin-4-one in good yield. This intermediate was brominated using bromine in acetic acid to give 3-bromo-2-methyl-4H-pyrido[1,2-a]pyrimidin-4-ones in good yield. All the intermediates prepared in this manner were characterized by spectral and analytical methods before using them for the preparation of compounds of invention.

Sources & evidence

ORD record
ord-642815646c0f4d5588b9a384b0f9566a
Source dataset
uspto-grants-2013_01
Patent number
US08349846B2

Reaction notes

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