Methanol → 4-(3-chlorophenyl)-1-ethyl-7-(1,1-dimethoxyethyl)pyrido[2,3-d]pyrimidin-2(1H)-one

HRID 368994Notes

Reaction equation

HRID 368994 reaction equation
[C:1]([C:4]1[CH:5]=[CH:6][C:7]2[C:12]([C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([Cl:19])[CH:14]=3)=[N:11][C:10](=[O:20])[N:9]([CH2:21][CH3:22])[C:8]=2[N:23]=1)(=[O:3])[CH3:2].[CH:24]([O-])([O-])[O:25]C.[CH3:29]O>>[Cl:19][C:15]1[CH:14]=[C:13]([C:12]2[C:7]3[CH:6]=[CH:5][C:4]([C:1]([O:25][CH3:24])([O:3][CH3:29])[CH3:2])=[N:23][C:8]=3[N:9]([CH2:21][CH3:22])[C:10](=[O:20])[N:11]=2)[CH:18]=[CH:17][CH:16]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 23284488HCID 23284488, compoundHCID 53629101Methylorthoformate

Product 1

HCID 232844984-(3-chlorophenyl)-1-ethyl-7-(1,1-dimethoxyethyl)pyrido[2,3-d]pyrimidin-2(1H)-oneYield 69%

Procedure

7-Acetyl-4-(3-chlorophenyl)-1-ethylpyrido[2,3-d]pyrimidin-2(1H)-one (1.62 g, 495 mmol) and 30 ml of methyl orthoformate were dissolved in 30 ml of methanol, a catalytically effective amount of Dowex-50W-X4 was added thereto, followed by heating overnight under reflux. After cooling to room temperature, insoluble matter was removed by filtration and the solvent was evaporated under a reduced pressure. The resulting residue was purified by silica gel column chromatography (toluene-ethyl acetate) and recrystallized from diisopropyl ether to give 1.27 g (69%) of 4-(3-chlorophenyl)-1-ethyl-7-(1,1-dimethoxyethyl)pyrido[2,3-d]pyrimidin-2(1H)-one.

Workup

  1. additiona catalytically effective amount of Dowex-50W-X4 was added
  2. temperatureby heating overnight
  3. temperatureunder reflux
  4. custominsoluble matter was removed by filtration
  5. customthe solvent was evaporated under a reduced pressure
  6. customThe resulting residue was purified by silica gel column chromatography (toluene-ethyl acetate)
  7. customrecrystallized from diisopropyl ether

Sources & evidence

ORD record
ord-bcaa6c13a9464b0a8212c7da803790dc
Source dataset
uspto-grants-2000_10
Patent number
US06136810

Reaction notes

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