Acetic Acid → HCID 135749804, compound

HRID 326866Notes

Reaction equation

HRID 326866 reaction equation
N[C:2]1[C:11]2[C:6](=[N:7][CH:8]=[CH:9][N:10]=2)[N:5]=[C:4]([CH2:12][O:13][CH2:14][CH2:15][OH:16])[N:3]=1.[C:17](O)(=[O:19])[CH3:18].[OH-:21].[Na+]>>[C:17]([O:16][CH2:15][CH2:14][O:13][CH2:12][C:4]1[NH:3][C:2](=[O:21])[C:11]2[C:6](=[N:7][CH:8]=[CH:9][N:10]=2)[N:5]=1)(=[O:19])[CH3:18]

Participants

4

Reactant 3

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 14880142HCID 14880142, compound

Product 1

HCID 135749804HCID 135749804, compound

Procedure

A solution of 10.0 g (0.0452 mole) of 4-amino-2-[(2-hydroxyethoxy)methyl]pteridine in 350 ml of 5% aqueous sodium hydroxide is brought gradually to 85° C and maintained at this temperature for 1 hour 30 minutes. After cooling, the solution obtained is acidified with acetic acid to pH 5.5, and is then concentrated to dryness under reduced pressure. The residue is taken up in 500 ml of isopropanol. The insoluble inorganic portion is removed by filtration. The isopropanolic solution is concentrated to dryness under reduced pressure. The solid residue is treated with 250 ml of acetic anhydride and this mixture is refluxed for 1 hour. After cooling, inorganic salts are removed by filtration; the filtrate is concentrated to dryness under reduced pressure. The residue is purified by 4 successive recrystallizations from ethanol in the presence of Norit. Yld: 1.2 g (10%), m.p. 157°-159° C.

Workup

  1. customis brought gradually to 85° C
  2. temperaturemaintained at this temperature for 1 hour 30 minutes
  3. temperatureAfter cooling
  4. customthe solution obtained
  5. concentrationis then concentrated to dryness under reduced pressure
  6. customThe insoluble inorganic portion is removed by filtration
  7. concentrationThe isopropanolic solution is concentrated to dryness under reduced pressure
  8. additionThe solid residue is treated with 250 ml of acetic anhydride
  9. temperaturethis mixture is refluxed for 1 hour
  10. temperatureAfter cooling
  11. custominorganic salts are removed by filtration
  12. concentrationthe filtrate is concentrated to dryness under reduced pressure
  13. customThe residue is purified by 4 successive recrystallizations from ethanol in the presence of Norit

Sources & evidence

ORD record
ord-69defecf25794b2b9a922984393e0158
Source dataset
uspto-grants-1993_12
Patent number
US05270465

Reaction notes

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