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

HRID 548778Notes

Reaction equation

HRID 548778 reaction equation
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]

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-8fd825978e9b4b0da81378823ff4d0e4
Source dataset
uspto-grants-2011_05
Patent number
US07943625B2

Reaction notes

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