Formic Acid → 3-(4-Methoxybenzyl)-2-thioxanthine

HRID 31073Notes

Reaction equation

[NH2:1][C:2]1[C:3](=[O:19])[NH:4][C:5](=[S:18])[N:6]([CH2:9][C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=2)[C:7]=1[NH2:8].[CH:20](O)=O>>[CH3:17][O:16][C:13]1[CH:12]=[CH:11][C:10]([CH2:9][N:6]2[C:7]3[N:8]=[CH:20][NH:1][C:2]=3[C:3](=[O:19])[NH:4][C:5]2=[S:18])=[CH:15][CH:14]=1

Participants

Reactant 2

HCID 284Formic Acid

HCID 86601064HCID 86601064, compound

Product 1

HCID 100169653-(4-Methoxybenzyl)-2-thioxanthineYield 16%

Conditions

Temperature: 100 °C

Procedure

5,6-Diamino-1-(4-methoxybenzyl)-2-thioxo-2,3-dihydro-1H-pyrimidin-4-one (0.83 g, 3.0 mmol) was dissolved in formic acid (3.0 mL) and the resulting solution heated at 100° C. for 1 h. The excess formic acid was removed under reduced pressure and the residue dissolved in 10% potassium hydroxide solution (8 mL) and heated at 100° C. for 15 minutes. The reaction mixture was neutralized with 10% acetic acid and the resulting precipitate collected by filtration. The precipitate was recrystallised from ethanol: dimethylformamide and the isolated crystals dissolved in 1M potassium hydroxide solution, precipitated by neutralization with 10% acetic acid and collected by filtration. After drying, the title compound (0.14 g, 16%) was obtained.

Workup

customThe excess formic acid was removed under reduced pressure
dissolutionthe residue dissolved in 10% potassium hydroxide solution (8 mL)
temperatureheated at 100° C. for 15 minutes
filtrationthe resulting precipitate collected by filtration
customThe precipitate was recrystallised from ethanol
dissolutiondimethylformamide and the isolated crystals dissolved in 1M potassium hydroxide solution
customprecipitated by neutralization with 10% acetic acid
filtrationcollected by filtration
customAfter drying

Sources & evidence

ORD record: ord-d7bf419e703049eb99939391f6d301e2
Source dataset: uspto-grants-2008_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07425560B2

Reaction notes

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