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

HRID 430505ノート

反応式

HRID 430505 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-2c43673865714184b49a81c5aac98e77
出典データセット
uspto-grants-2001_11
特許番号
US06323208B1

反応ノート

読み込み中…