3-[(2-Methyl-4-oxo-4H-chromen-8-yl)methylene]pentane-2,4-dione → 6-Acetyl-7-methyl-5-(2-methyl-4-oxo-4H-chromen-8-yl)-5,8-dihydropyrido[2,3-d]pyrimidin-4(3H)-one

HRID 1947243Notes

Reaction equation

HRID 1947243 reaction equation
[CH3:1][C:2]1[O:3][C:4]2[C:9]([C:10](=[O:12])[CH:11]=1)=[CH:8][CH:7]=[CH:6][C:5]=2[CH:13]=[C:14]([C:18](=[O:20])[CH3:19])[C:15](=O)[CH3:16].[NH2:21][C:22]1[N:27]=[CH:26][NH:25][C:24](=[O:28])[CH:23]=1>C(O)(C)C>[C:18]([C:14]1[CH:13]([C:5]2[CH:6]=[CH:7][CH:8]=[C:9]3[C:4]=2[O:3][C:2]([CH3:1])=[CH:11][C:10]3=[O:12])[C:23]2[C:24](=[O:28])[NH:25][CH:26]=[N:27][C:22]=2[NH:21][C:15]=1[CH3:16])(=[O:20])[CH3:19]

Participants

4

Reactant 2

HCID 591869153-[(2-Methyl-4-oxo-4H-chromen-8-yl)methylene]pentane-2,4-dioneHCID 1354312726-Amino-1H-pyrimidin-4-one

Product 1

HCID 1361308496-Acetyl-7-methyl-5-(2-methyl-4-oxo-4H-chromen-8-yl)-5,8-dihydropyrido[2,3-d]pyrimidin-4(3H)-one

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

500 mg (1.85 mmol) of 3-[(2-methyl-4-oxo-4H-chromen-8-yl)methylene]pentane-2,4-dione are mixed with 308 mg (2.77 mmol) of 6-aminopyrimidin-4(3H)-one, dissolved in 10 ml of isopropanol and heated under reflux under argon for 2 days. The mixture is then concentrated and the residue is recrystallized from methanol. 341 mg (51% of theory) of the title compound are obtained as a yellow solid.

Workup

  1. temperatureheated
  2. temperatureunder reflux under argon for 2 days
  3. concentrationThe mixture is then concentrated
  4. customthe residue is recrystallized from methanol

Sources & evidence

ORD record
ord-e59d48c1ff444ab89aa65002008ea8ba
Source dataset
uspto-grants-2013_03
Patent number
US08399471B2

Reaction notes

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