4-Fluoroaniline → 2-Ethyl-3-(4-fluorophenyl)pyrido[2,3-d]pyrimidin-4(3H)-one

HRID 1264909Notes

Reaction equation

HRID 1264909 reaction equation
[CH2:1]([C:3]1O[C:5](=[O:13])[C:6]2[CH:12]=[CH:11][CH:10]=[N:9][C:7]=2[N:8]=1)[CH3:2].[F:14][C:15]1[CH:21]=[CH:20][C:18]([NH2:19])=[CH:17][CH:16]=1>C1(C)C=CC=CC=1>[CH2:1]([C:3]1[N:19]([C:18]2[CH:20]=[CH:21][C:15]([F:14])=[CH:16][CH:17]=2)[C:5](=[O:13])[C:6]2[CH:12]=[CH:11][CH:10]=[N:9][C:7]=2[N:8]=1)[CH3:2]

Participants

4

Reactant 2

HCID 97314-FluoroanilineHCID 186137472-Ethyl-4H-pyrido[2,3-d][1,3]oxazin-4-one

Product 1

HCID 186137392-Ethyl-3-(4-fluorophenyl)pyrido[2,3-d]pyrimidin-4(3H)-oneYield 32%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
120 °C

Procedure

A suspension of the pyrido-oxazine (16) (0.5 g, 2.84 mmol) and 4-fluoroaniline (0.32 g, 2.84 mmol) in toluene (21 mL) was heated to reflux overnight. The solution was concentrated to dryness under reduced pressure and ethylene glycol (2 mL) and sodium hydroxide (5 mg) were added. The mixture was heated again to 120° C. for 4 h, and the ethylene glycol was distilled off under reduced pressure. The resulting dark brown solid was subjected to silica-gel column chromatography [eluent: Ethyl acetate:Hexane, 20:80, v/v→100:0, v/v] to give the title pyrido-pyrimidinone (17) (244 mg, 32%) as a beige solid:

Workup

  1. temperaturewas heated
  2. temperatureto reflux overnight
  3. concentrationThe solution was concentrated to dryness under reduced pressure and ethylene glycol (2 mL) and sodium hydroxide (5 mg)
  4. additionwere added
  5. distillationthe ethylene glycol was distilled off under reduced pressure

Sources & evidence

ORD record
ord-880af88b750e49a3bcb7a9499853eb9d
Source dataset
uspto-grants-2003_04
Patent number
US06545005B1

Reaction notes

Loading…