4-(3-chlorophenyl)-1-ethyl-7-(1-hydroxyethyl)pyrido[2,3-d]pyrimidin-2(1H)-one → HCID 23284488, compound

HRID 368988Notes

Reaction equation

HRID 368988 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[C:9]3[CH:20]=[CH:19][C:18]([CH:21]([OH:23])[CH3:22])=[N:17][C:10]=3[N:11]([CH2:15][CH3:16])[C:12](=[O:14])[N:13]=2)[CH:5]=[CH:6][CH:7]=1>C(Cl)(Cl)Cl.[O-2].[O-2].[Mn+4]>[C:21]([C:18]1[CH:19]=[CH:20][C:9]2[C:8]([C:4]3[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=3)=[N:13][C:12](=[O:14])[N:11]([CH2:15][CH3:16])[C:10]=2[N:17]=1)(=[O:23])[CH3:22]

Participants

4

Reactant 1

HCID 232844934-(3-chlorophenyl)-1-ethyl-7-(1-hydroxyethyl)pyrido[2,3-d]pyrimidin-2(1H)-one

Product 1

HCID 23284488HCID 23284488, compoundYield 84%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalyst3×HCID 6212ChloroformSolvent

Procedure

Manganese dioxide (1.00 g) was added to a solution of 366 mg (1.1 mmol) of 4-(3-chlorophenyl)-1-ethyl-7-(1-hydroxyethyl)pyrido[2,3-d]pyrimidin-2(1H)-one dissolved in 20 ml of chloroform, and the mixture was heated under reflux for 1 hour. The reaction solution was mixed with 1.00 g of manganese dioxide and heated under reflux for 1 hour and then again mixed with 500 mg of manganese dioxide and heated under reflux for 1 hour. After removing insoluble matter by filtration, the filtrate was concentrated under a reduced pressure and the resulting residue was purified by silica gel column chromatography (hexane-ethyl acetate-chloroform) to give 303 mg of 7-acetyl-4-(3-chlorophenyl)-1-ethylpyrido[2,3-d]pyrimidin-2(1H)-one. The yield was 84%.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 1 hour
  3. temperatureheated
  4. temperatureunder reflux for 1 hour
  5. temperatureheated
  6. temperatureunder reflux for 1 hour
  7. customAfter removing insoluble matter
  8. filtrationby filtration
  9. concentrationthe filtrate was concentrated under a reduced pressure
  10. customthe resulting residue was purified by silica gel column chromatography (hexane-ethyl acetate-chloroform)

Sources & evidence

ORD record
ord-10cf139cb3af4a718c9430b5336ecfa2
Source dataset
uspto-grants-2000_10
Patent number
US06136810

Reaction notes

Loading…