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

HRID 227609노트

반응식

HRID 227609 반응식
[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

참가 물질

6

반응물 2

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

생성물 1

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

시약·촉매·용매 3

HCID 23925Iron촉매HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-f23060ba9910479984dc57b40ae9d09e
출처 데이터셋
uspto-grants-2009_07
특허 번호
US07560552B2

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