Formic Acid → HCID 23627929, compound

HRID 548786Notes

Reaction equation

HRID 548786 reaction equation
[NH2:1][C:2]1[C:3](=[O:16])[NH:4][C:5](=[S:15])[N:6]([CH2:9][CH:10]([O:12][CH2:13][CH3:14])[CH3:11])[C:7]=1[NH2:8].[CH:17](O)=O>>[CH2:13]([O:12][CH:10]([CH3:11])[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])[CH3:14]

Participants

3

Reactant 2

HCID 284Formic AcidHCID 86623123HCID 86623123, compound

Product 1

HCID 23627929HCID 23627929, compoundYield 29%

Conditions

Temperature
70 °C

Procedure

5,6-Diamino-1-(2-ethoxy-propyl)-2-thioxo-2,3-dihydro-1H-pyrimidin-4-one (0.60 g, 2.45 mmol) obtained from Example 5(d) was suspended in formic acid (6 mL) and the obtained solution was heated at 70° C. for 2 h. Excess formic acid was evaporated off under reduced pressure. 10% sodium hydroxide (6 mL) was added to the solid and the obtained solution was heated at 70° C. for 2 h. The pH of the solution was adjusted to neutral pH with 2M sulphuric acid. The obtained precipitate was collected by filtration and washed with water. Purified by preparative HPLC, the title compound (0.18 g, 29% yield) was obtained as a solid.

Workup

  1. customExcess formic acid was evaporated off under reduced pressure
  2. addition10% sodium hydroxide (6 mL) was added to the solid
  3. temperaturethe obtained solution was heated at 70° C. for 2 h
  4. filtrationThe obtained precipitate was collected by filtration
  5. washwashed with water
  6. customPurified by preparative HPLC

Sources & evidence

ORD record
ord-7d3f9e0bbd2b4cb3aa94600a92b469c6
Source dataset
uspto-grants-2011_05
Patent number
US07943625B2

Reaction notes

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