Ethanol → 5-(4-Aminophenyl)thieno[2,3-d]pyrimidin-4-amine

HRID 227609ノート

反応式

HRID 227609 の反応式
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[C:18]3[C:17]([NH2:19])=[N:16][CH:15]=[N:14][C:13]=3[S:12][CH:11]=2)=[CH:6][CH:5]=1)([O-])=O.C(O)C>C1COCC1.O.[Fe]>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([C:10]2[C:18]3[C:17]([NH2:19])=[N:16][CH:15]=[N:14][C:13]=3[S:12][CH:11]=2)=[CH:8][CH:9]=1

参加物

6

反応物 2

HCID 702EthanolHCID 597942485-(4-Nitrophenyl)thieno[2,3-d]pyrimidin-4-amine

生成物 1

HCID 250237745-(4-Aminophenyl)thieno[2,3-d]pyrimidin-4-amine収率 97.4%

試薬・触媒・溶媒 3

HCID 23925Iron触媒HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

A suspension of Example 58C (0.5 g, 1.83 mmol) in THF (30 mL), water (15 mL), and ethanol (40 mL) was heated to 50° C., treated with iron powder (0.616 g, 11.02 mmol), heated to between 70 and 80° C. for two hours, and filtered while hot through diatomaceous earth (Celite®). The pad was washed with TBF (10 mL) and ethanol and the combined filtrates were concentrated. The residue was partitioned between water and ethyl acetate and the aqueous phase was extracted three times with ethyl acetate. The combined extracts were washed with brine, dried (MgSO4), filtered, and concentrated to give 0.432 g of the desired product. MS (CI) m/e 243 (M+H)+; 1H NMR (300 MHz, DMSO-d6) δ 8.30 (s, 1H); 7.28 (s, 1H); 7.11 (d, J=8.4 Hz, 2H); 6.68 (d, J=8.4 Hz, 2H); 5.39 (br s, 2H).

後処理

  1. temperatureheated to between 70 and 80° C. for two hours
  2. filtrationfiltered while hot through diatomaceous earth (Celite®)
  3. washThe pad was washed with TBF (10 mL) and ethanol
  4. concentrationthe combined filtrates were concentrated
  5. customThe residue was partitioned between water and ethyl acetate
  6. extractionthe aqueous phase was extracted three times with ethyl acetate
  7. washThe combined extracts were washed with brine
  8. dry with materialdried (MgSO4)
  9. filtrationfiltered
  10. concentrationconcentrated

出典と根拠

ORDレコード
ord-f23060ba9910479984dc57b40ae9d09e
出典データセット
uspto-grants-2009_07
特許番号
US07560552B2

反応ノート

読み込み中…