Formic Acid → 2-Thioxanthine, TX3

HRID 31068Notes

Reaction equation

HRID 31068 reaction equation
[NH2:1][C:2]1[C:3](=[O:16])[NH:4][C:5](=[S:15])[N:6]([CH2:9][CH:10]2[CH2:14][CH2:13][CH2:12][O:11]2)[C:7]=1[NH2:8].[CH:17](O)=O>>[O:11]1[CH2:12][CH2:13][CH2:14][CH:10]1[CH2:9][N:6]1[C:7]2[N:8]=[CH:17][NH:1][C:2]=2[C:3](=[O:16])[NH:4][C:5]1=[S:15]

Participants

3

Reactant 2

HCID 284Formic AcidHCID 86601059HCID 86601059, compound

Product 1

HCID 103548422-Thioxanthine, TX3Yield 87%

Conditions

Temperature
70 °C

Procedure

5,6-Diamino-1-(2-tetrahydrofuryl-methyl)-2-thioxo-2,3-dihydro-1H-pyrimidin-4-one (0.25 g, 1.0 mmol) was dissolved in formic acid (1 mL) and heated at 70° C. for 0.5 h. After a few minutes a pink solid formed in the solution. The excess of formic acid was evaporated off and the resulting solid dissolved in 10% sodium hydroxide solution (4 mL). This solution was heated at 70° C. for 40 minutes, then neutralized with 2M hydrochloric acid. The resulting precipitate was collected by filtration, washed with water and dried, giving pure product (0.23 g, 87%).

Workup

  1. customAfter a few minutes a pink solid formed in the solution
  2. customThe excess of formic acid was evaporated off
  3. dissolutionthe resulting solid dissolved in 10% sodium hydroxide solution (4 mL)
  4. temperatureThis solution was heated at 70° C. for 40 minutes
  5. filtrationThe resulting precipitate was collected by filtration
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-b99b08c9630f41409022163988c76335
Source dataset
uspto-grants-2008_09
Patent number
US07425560B2

Reaction notes

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