Acetic Anhydride → 2-[2-(2-Fluoro-phenyl)-vinyl]-3-o-tolyl-3H-pteridin-4-one

HRID 430505노트

반응식

HRID 430505 반응식
[CH3:1][C:2]1[N:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[CH3:18])[C:10](=[O:19])[C:9]2[C:4](=[N:5][CH:6]=[CH:7][N:8]=2)[N:3]=1.[F:20][C:21]1[CH:28]=[CH:27][CH:26]=[CH:25][C:22]=1[CH:23]=O.C(OC(=O)C)(=O)C>O1CCOCC1>[F:20][C:21]1[CH:28]=[CH:27][CH:26]=[CH:25][C:22]=1[CH:23]=[CH:1][C:2]1[N:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[CH3:18])[C:10](=[O:19])[C:9]2[C:4](=[N:5][CH:6]=[CH:7][N:8]=2)[N:3]=1

참가 물질

5

반응물 3

HCID 7918Acetic AnhydrideHCID 67970o-FluorobenzaldehydeHCID 2107974(3H)-Pteridinone, 2-methyl-3-(o-tolyl)-

생성물 1

HCID 697092452-[2-(2-Fluoro-phenyl)-vinyl]-3-o-tolyl-3H-pteridin-4-one수율 55.4%

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

실험 절차

A mixture of fused zinc chloride (0.17 g, 1.25 mmol), dioxane (15 mL), 2-methyl-3-(2-methyl-phenyl)-3H-pteridin-4-one (0.174 g, 0.69 mmol, preparation 8), and 2-fluorobenzaldehyde (0.22 mL, 2.07 mmol), and acetic anhydride 0.195 mL, 2.07 mmol) was refluxed overnight. The reaction was cooled and concentrated. The residual material was partitioned between saturated aqueous sodium bicarbonate and methylene chloride. The layers were carefully shaken and separated. The organic layer was washed with brine, dried and concentrated. The residue was flash chromatographed on silica gel (0.75×4 inches) with elution proceeding as follows: 50% ethyl acetate/hexane (300 mL), forerun; 60% ethyl acetate/hexane (400 mL). 2-[2-(2-Fluoro-phenyl)-vinyl]-3-o-tolyl-3H-pteridin-4-one (0.137 g, 55%) was isolated as a yellow crystalline solid. A sample was recrystallized from ethyl acetate.

후처리

  1. temperaturewas refluxed overnight
  2. temperatureThe reaction was cooled
  3. concentrationconcentrated
  4. customThe residual material was partitioned between saturated aqueous sodium bicarbonate and methylene chloride
  5. customseparated
  6. washThe organic layer was washed with brine
  7. customdried
  8. concentrationconcentrated
  9. customchromatographed on silica gel (0.75×4 inches) with elution proceeding

출처 및 근거

ORD 기록
ord-2c43673865714184b49a81c5aac98e77
출처 데이터셋
uspto-grants-2001_11
특허 번호
US06323208B1

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