Ethyl isothiocyanatoformate → 3-(2-Ethoxy-2-methylpropyl)-2-thioxanthine

HRID 548778노트

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HRID 548778 반응식
C(O[C:4]([N:6]=[C:7]=[S:8])=[O:5])C.[CH2:9]([O:11][C:12]([CH3:24])([CH3:23])[CH2:13][NH:14][C:15]1[N:16]=[CH:17][NH:18][C:19]=1C(N)=O)[CH3:10]>C(Cl)Cl>[CH2:9]([O:11][C:12]([CH3:23])([CH3:24])[CH2:13][N:14]1[C:15]2[N:16]=[CH:17][NH:18][C:19]=2[C:4](=[O:5])[NH:6][C:7]1=[S:8])[CH3:10]

참가 물질

4

반응물 2

HCID 85320Ethyl isothiocyanatoformateHCID 671575334-[(2-ethoxy-2-methylpropyl)amino]-1H-imidazole-5-carboxamide

생성물 1

HCID 236583743-(2-Ethoxy-2-methylpropyl)-2-thioxanthine수율 47%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

Ethoxycarbonyl isothiocyanate (0.171 g, 1.30 mmol) was added to a stirred solution of 4-[(2-Ethoxy-2-methylpropyl)amino]-1H-imidazole-5-carboxamide (0.246 g, 1.09 mmol), which had been obtained from Example 1(c), in CH2Cl2 (1.1 mL) at r.t. for 0.5 h, then the reaction was left unstirred at 4° C. for 16 h. The reaction mixture was heated to r.t. for 1 h and the solvent was evaporated, the residue was dissolved in 2% sodium hydroxide (aq.) (27 mL) and the reaction was heated at 50° C. for 5.5 h. The pH was adjusted to neutral with conc. HCl and 1M HCl. The precipitate was collected by filtration, washed with water and purified by flash silica gel chromatography (CHCl3/MeOH; 20:1), to give the title compound in 47% yield (96 mg).

후처리

  1. customthe solvent was evaporated
  2. dissolutionthe residue was dissolved in 2% sodium hydroxide (aq.) (27 mL)
  3. temperaturethe reaction was heated at 50° C. for 5.5 h
  4. filtrationThe precipitate was collected by filtration
  5. washwashed with water
  6. custompurified by flash silica gel chromatography (CHCl3/MeOH; 20:1)

출처 및 근거

ORD 기록
ord-8fd825978e9b4b0da81378823ff4d0e4
출처 데이터셋
uspto-grants-2011_05
특허 번호
US07943625B2

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