Formic Acid → HCID 24855434, compound

HRID 912648Notes

Reaction equation

HRID 912648 reaction equation
[NH2:1][C:2]1[C:3](=[O:17])[NH:4][C:5](=[S:16])[N:6]([CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=2)[C:7]=1[NH2:8].[CH:18](O)=O>>[N:11]1[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=1[CH2:9][N:6]1[C:7]2[N:8]=[CH:18][NH:1][C:2]=2[C:3](=[O:17])[NH:4][C:5]1=[S:16]

Participants

3

Reactant 2

HCID 284Formic AcidHCID 86631108HCID 86631108, compound

Product 1

HCID 24855434HCID 24855434, compoundYield 20%

Conditions

Temperature
70 °C

Procedure

5,6-Diamino-1-(pyridin-2-ylmethyl)-2-thioxo-2,3-dihydro-1H-pyrimidin-4-one (0.33 g, 1.3 mmol, obtained from Example 1(c)) in formic acid was heated at 70° C. for 30 minutes. The excess of formic acid was evaporated in vacuo. Sodium hydroxide (10% aq., 2 mL) was added to the residue and the reaction mixture was heated at 70° C. for 1 h. The mixture was then diluted with water (20 mL) and neutralized using 2M sulfuric acid. The precipitated solid was collected by filtration, washed with water and dried. The crude product was purified by preparative HPLC, giving the title compound (0.068 g, 20%) as a solid.

Workup

  1. customThe excess of formic acid was evaporated in vacuo
  2. additionSodium hydroxide (10% aq., 2 mL) was added to the residue
  3. additionThe mixture was then diluted with water (20 mL)
  4. filtrationThe precipitated solid was collected by filtration
  5. washwashed with water
  6. customdried
  7. customThe crude product was purified by preparative HPLC

Sources & evidence

ORD record
ord-ddd6b21185bf4864bee406eed040050c
Source dataset
uspto-grants-2011_09
Patent number
US08026244B2

Reaction notes

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