Hydrochloric Acid → 4-(1-Methyl-2,6-dioxo-1,2,6,7-tetrahydro-3H-purin-3-yl)butanoic acid

HRID 443970Notes

Reaction equation

HRID 443970 reaction equation
[CH3:1][N:2]1[C:11](=[O:12])[C:10]2[N:9](COC(=O)C(C)(C)C)[CH:8]=[N:7][C:6]=2[N:5]([CH2:21][CH2:22][CH2:23][C:24]([O:26]CC)=[O:25])[C:3]1=[O:4].Cl>[OH-].[Na+]>[CH3:1][N:2]1[C:11](=[O:12])[C:10]2[NH:9][CH:8]=[N:7][C:6]=2[N:5]([CH2:21][CH2:22][CH2:23][C:24]([OH:26])=[O:25])[C:3]1=[O:4]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 128798421-Methyl-3(carboethoxypropyl)-7-(pivaloyloxymethyl)xanthine

Product 1

HCID 128798434-(1-Methyl-2,6-dioxo-1,2,6,7-tetrahydro-3H-purin-3-yl)butanoic acid

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

An oily suspension of 1-methyl-3(carboethoxypropyl)-7-(pivaloyloxymethyl)xanthine (508 mg) in 2N NaOH (36.2 ml) was heated under nitrogen at 95°-100° for 2 hrs. The oil dissolved and the reaction was shown to be complete by TLC. After cooling the reaction mixure, it was acidified to pH 2-3 with 15 ml 12% hydrochloric acid and the solution extracted with 3×5 ml chloroform to remove the pivalic acid. After washing the chloroform extracts with 5 ml 0.5N HCl, aqueous solutions were combined and stripped to dryness and the residue dried in vacuo at room temperature. The crude product was dissolved in about 22 ml hot water, decolorized and concentrated to 15 ml, at which time 159 mg of a crystalline product was obtained upon cooling. m.p. 220°-221°.

Workup

  1. temperaturewas heated under nitrogen at 95°-100° for 2 hrs
  2. dissolutionThe oil dissolved
  3. temperatureAfter cooling the reaction mixure, it
  4. extractionthe solution extracted with 3×5 ml chloroform
  5. customto remove the pivalic acid
  6. washAfter washing the chloroform
  7. customthe residue dried in vacuo at room temperature
  8. dissolutionThe crude product was dissolved in about 22 ml hot water
  9. concentrationdecolorized and concentrated to 15 ml, at which time 159 mg of a crystalline product
  10. customwas obtained
  11. temperatureupon cooling

Sources & evidence

ORD record
ord-548efce52155466ca0a80a042c2d8022
Source dataset
uspto-grants-1981_04
Patent number
US04262089

Reaction notes

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