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

HRID 705111ノート

反応式

HRID 705111 の反応式
[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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

反応条件

温度
120 °C

実験手順

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, ν/ν->100:0, ν/ν] to give the title pyrido-pyrimidinone (17) (244 mg, 32%) as a beige solid:

後処理

  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

出典と根拠

ORDレコード
ord-f4c5bd01be1e4a3aabb449d281fcc8fe
出典データセット
uspto-grants-2015_11
特許番号
US09173869B2

反応ノート

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