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

HRID 548782Notes

Reaction equation

C(O[C:4]([N:6]=[C:7]=[S:8])=[O:5])C.[CH3:9][O:10][C:11]([CH3:23])([CH3:22])[CH2:12][NH:13][C:14]1[N:15]=[CH:16][NH:17][C:18]=1C(N)=O>C(Cl)Cl>[CH3:9][O:10][C:11]([CH3:23])([CH3:22])[CH2:12][N:13]1[C:14]2[N:15]=[CH:16][NH:17][C:18]=2[C:4](=[O:5])[NH:6][C:7]1=[S:8]

Participants

Conditions

Temperature: 50 °C

Procedure

Ethoxycarbonyl isothiocyanate (0.144 g, 1.1 mmol) was added to a stirred solution of 4-[(2-methoxy-2-methylpropyl)amino]-1H-imidazole-5-carboxamide (0.155 g, 0.73 mmol), which was obtained from Example 3(b), in CH2Cl2 (2.5 mL) at r.t. for 16 h. The solvent was evaporated and the residue was then dissolved in 2% aqueous sodium hydroxide (NaOH) solution (10 mL) and heated at 50° C. for 3 h. The pH was adjusted to neutral with 2 M HCl and the resulted precipitates were collected by filtration followed by prep-HPLC purification. The title compound was obtained as a white solid in 32% yield (60 mg).

Workup

customThe solvent was evaporated
dissolutionthe residue was then dissolved in 2% aqueous sodium hydroxide (NaOH) solution (10 mL)
customthe resulted precipitates
filtrationwere collected by filtration
customfollowed by prep-HPLC purification

Sources & evidence

ORD record: ord-c900137f21a04bed8761c60fe3fdd23e
Source dataset: uspto-grants-2011_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07943625B2

Reaction notes

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