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

HRID 705111노트

반응식

HRID 705111 반응식
[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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 1140Toluene용매

반응 조건

온도
120 °C

실험 절차

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:

후처리

  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

출처 및 근거

ORD 기록
ord-f4c5bd01be1e4a3aabb449d281fcc8fe
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09173869B2

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