Phosphorus trichloride → HCID 18350679、化合物

HRID 430511

反応式

HRID 430511 の反応式
[NH2:1][C:2]1[C:3]([Cl:8])=[N:4][CH:5]=[CH:6][CH:7]=1.[C:9]([NH:12][C:13]1[CH:17]=[CH:16][S:15][C:14]=1[C:18](O)=[O:19])(=O)[CH3:10].P(Cl)(Cl)Cl>N1C=CC=CC=1>[CH3:10][C:9]1[N:1]([C:2]2[C:3]([Cl:8])=[N:4][CH:5]=[CH:6][CH:7]=2)[C:18](=[O:19])[C:14]2[S:15][CH:16]=[CH:17][C:13]=2[N:12]=1

参加物

5

反応物 3

HCID 24387Phosphorus trichlorideHCID 805282-Chloro-3-pyridylamineHCID 28075793-Acetamidothiophene-2-carboxylic acid

生成物 1

HCID 18350679HCID 18350679、化合物収率 63%

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

反応条件

温度
105 °C

実験手順

To a mixture of pyridine (4 mL), 3-amino-2-chloropyridine (0.514 g, 4 mmol), and 3-acetamidothiophene-2-carboxylic acid (0.370 g, 4 mmol) was added phosphorus trichloride (0.02 mL, 2.3 mmol). The reaction was heated to 105° C. for 3 hours, cooled to ambient temperature and partitioned between ethyl acetate and water. Phases were separated and the aqueous layer was extracted with ethyl acetate. The combined organic phase was washed with water and brine, dried over sodium sulfate and concentrated to a greenish brown oil. This residue was flash chromatographed on silica gel (20×120 mm) eluting with 20-40% ethyl acetate/hexane to afford 0.350 g (63%) of 2-methyl-3-(2-chloropyrid-3-yl)-3H-thieno[3,2-d]pyrimidin-4-one as a yellow foam.

後処理

  1. temperaturecooled to ambient temperature
  2. custompartitioned between ethyl acetate and water
  3. customPhases were separated
  4. extractionthe aqueous layer was extracted with ethyl acetate
  5. washThe combined organic phase was washed with water and brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated to a greenish brown oil
  8. customchromatographed on silica gel (20×120 mm)
  9. washeluting with 20-40% ethyl acetate/hexane

出典と根拠

ORDレコード
ord-2d0269e9bbed4ddebd146f92e46f6348
出典データセット
uspto-grants-2001_11
特許番号
US06323208B1

関連ノート

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