Formic Acid → 3-Isobutyl-7-methyl-2-thioxanthine

HRID 883547Notes

Reaction equation

HRID 883547 reaction equation
[NH2:1][C:2]1[N:7]([CH2:8][CH:9]([CH3:11])[CH3:10])[C:6](=[S:12])[NH:5][C:4](=[O:13])[C:3]=1[NH:14][CH3:15].[CH:16](O)=O>>[CH2:8]([N:7]1[C:2]2[N:1]=[CH:15][N:14]([CH3:16])[C:3]=2[C:4](=[O:13])[NH:5][C:6]1=[S:12])[CH:9]([CH3:11])[CH3:10]

Participants

3

Reactant 2

HCID 284Formic AcidHCID 866010526-Amino-1-isobutyl-5-methylamino-2-thioxo-2,3-dihydro-1H-pyrimidin-4-one

Product 1

HCID 100144363-Isobutyl-7-methyl-2-thioxanthineYield 74%

Conditions

Temperature
85 °C

Procedure

6-Amino-1-isobutyl-5-methylamino-2-thioxo-2,3-dihydro-1H-pyrimidin-4-one (0.11 g, 0.48 mmol) was dissolved in formic acid (1 mL) and heated at 85° C. for 1 h. The excess of formic acid was evaporated off under reduced pressure. 10% Sodium hydroxide solution (2 mL) was added and the solution was heated at 85° C. for 20 minutes. Water was added and the pH was adjusted to 4 with dilute acetic acid, upon which a white solid precipitated. The white solid was collected by filtration, washed with water and dried to yield the title compound (85 mg, 74%).

Workup

  1. customThe excess of formic acid was evaporated off under reduced pressure
  2. addition10% Sodium hydroxide solution (2 mL) was added
  3. temperaturethe solution was heated at 85° C. for 20 minutes
  4. additionWater was added
  5. customprecipitated
  6. filtrationThe white solid was collected by filtration
  7. washwashed with water
  8. customdried

Sources & evidence

ORD record
ord-46a185f129f449799216a08bbc70407c
Source dataset
uspto-grants-2012_08
Patent number
US08236951B2

Reaction notes

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