Formamide → 3H,4H-thieno[3,2-d]pyrimidin-4-one

HRID 50842

반응식

HRID 50842 반응식
[NH2:1][C:2]1[CH:6]=[CH:5][S:4][C:3]=1[C:7]([O:9]C)=O.[CH:11]([NH2:13])=O>CCO>[N:1]1[C:2]2[CH:6]=[CH:5][S:4][C:3]=2[C:7](=[O:9])[NH:13][CH:11]=1

참가 물질

4

반응물 2

HCID 713FormamideHCID 89652Methyl 3-amino-2-thiophenecarboxylate

생성물 1

HCID 1354174223H,4H-thieno[3,2-d]pyrimidin-4-one수율 26%

시약·촉매·용매 1

HCID 702Ethanol용매

반응 조건

온도
240 °C

실험 절차

A mixture of methyl 3-aminothiophene-2-carboxylate (1 g, 6.3 mmol) and formamide (2 g) is heated at 240° C. for 10 min. Upon cooling a precipitate appeared. It is dissolved in EtOH and filtered. The filtrate is concentrated under reduced pressure and the residue is purified by silica gel chromatography eluting with 10% MeOH in CH2Cl2 to yield 3H-thieno[3,2-d]pyrimid-4-one (249 mg, 26%) as a solid. 1H NMR (DMSO) δ 12.61 (1H, brs), 8.20 (1H, s), 8.17 (1H, d, J=5 Hz), 7.42 (1H, d, J=5 Hz).

후처리

  1. temperatureUpon cooling a precipitate
  2. filtrationfiltered
  3. concentrationThe filtrate is concentrated under reduced pressure
  4. customthe residue is purified by silica gel chromatography
  5. washeluting with 10% MeOH in CH2Cl2

출처 및 근거

ORD 기록
ord-21551590b0f94b3e97926eeaf14e009e
출처 데이터셋
uspto-grants-2004_03
특허 번호
US06713484B2

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