Glycolic Acid → HCID 11438408, compound

HRID 2114604Notes

Reaction equation

HRID 2114604 reaction equation
[CH2:1]([N:8]1[C:15]([NH2:16])=[C:14]([NH2:17])[C:12](=[O:13])[N:11]([CH2:18][CH2:19][CH3:20])[C:9]1=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:21](O)(=O)[CH2:22][OH:23]>O1CCOCC1>[CH2:18]([N:11]1[C:12](=[O:13])[C:14]2[NH:17][C:21]([CH2:22][OH:23])=[N:16][C:15]=2[N:8]([CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[C:9]1=[O:10])[CH2:19][CH3:20]

Participants

4

Reactant 2

HCID 757Glycolic AcidHCID 11254336HCID 11254336, compound

Product 1

HCID 11438408HCID 11438408, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of the diamino-uracil derivative (from Example 5) (3.6 mmol), glycolic acid (7.3 mmol) and 1,4-dioxane (1 mL) was heated at 100° C. for 1 h. After cooling, a yellow solid precipitated from the solution and it was suspended in a mixture of H2O/EtOH 1:1 (20 mL). After basification with NaOH, the solution was heated at reflux for 3 hours, then cooled to 0° C. and acidified with acetic acid. The product precipitated as a white solid which was collected by filtration and dried. (White solid. Yield 70%).

Workup

  1. temperatureAfter cooling
  2. customa yellow solid precipitated from the solution and it
  3. additionwas suspended in a mixture of H2O/EtOH 1:1 (20 mL)
  4. temperatureAfter basification with NaOH, the solution was heated
  5. temperatureat reflux for 3 hours
  6. temperaturecooled to 0° C.
  7. customThe product precipitated as a white solid which
  8. filtrationwas collected by filtration
  9. customdried

Sources & evidence

ORD record
ord-d09efa53de364807adf57137477a5570
Source dataset
uspto-grants-2008_10
Patent number
US07435740B2

Reaction notes

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