Acetic Acid → 3-(4-hydroxyphenyl)-6-methoxy-2-methylpyrido[3,4-d]pyrimidin-4(3H)-one

HRID 2386967Notes

Reaction equation

HRID 2386967 reaction equation
Cl[C:2]1[N:20]=[CH:19][C:5]2[N:6]=[C:7]([CH3:18])[N:8]([C:11]3[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=3)[C:9](=[O:10])[C:4]=2[CH:3]=1.C[O-].[Na+].[C:24](O)(=[O:26])C>CO>[OH:17][C:14]1[CH:15]=[CH:16][C:11]([N:8]2[C:9](=[O:10])[C:4]3[CH:3]=[C:2]([O:26][CH3:24])[N:20]=[CH:19][C:5]=3[N:6]=[C:7]2[CH3:18])=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 10942334Sodium MethoxideHCID 231511466-chloro-2-methyl-3-(4-hydroxyphenyl)pyrido[3,4-d]pyrimidin-4(3H)-one

Product 1

HCID 231512043-(4-hydroxyphenyl)-6-methoxy-2-methylpyrido[3,4-d]pyrimidin-4(3H)-oneYield 88%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

6-chloro-3-(4-hydroxyphenyl)-2-methylpyrido[3,4-d]pyrimidin-4(3H)-one (300 mg, 1.04 mmol) was dissolved in dry methanol (15 mL) in a current of nitrogen, sodium methoxide (7 mmol) was added and the mixture was heated under reflux for 20 hours. After leaving to cool, acetic acid was added and the solvent was distilled off under reduced pressure. Distilled water was added to the residue, the solid precipitate was filtered off, and the title compound (259 mg, 88%) was thus obtained as a lavender color solid.

Workup

  1. additionwas added
  2. temperaturethe mixture was heated
  3. temperatureunder reflux for 20 hours
  4. customAfter leaving
  5. temperatureto cool
  6. distillationthe solvent was distilled off under reduced pressure
  7. additionDistilled water was added to the residue
  8. filtrationthe solid precipitate was filtered off

Sources & evidence

ORD record
ord-4cf5419600fe47ed907fd912dfd6d365
Source dataset
uspto-grants-2012_09
Patent number
US08268842B2

Reaction notes

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