Acetamide,N-(9-((2-(acetyloxy)-1-((acetyloxy)methyl)ethoxy)methyl)-6,9-dihydro-6-oxo-1H-purin-2-yl)- → Ganciclovir

HRID 1194796Notes

Reaction equation

HRID 1194796 reaction equation
C([NH:4][C:5]1[NH:6][C:7](=[O:27])[C:8]2[N:9]=[CH:10][N:11]([CH2:14][O:15][CH:16]([CH2:22][O:23]C(=O)C)[CH2:17][O:18]C(=O)C)[C:12]=2[N:13]=1)(=O)C>CN>[OH:18][CH2:17][CH:16]([O:15][CH2:14][N:11]1[CH:10]=[N:9][C:8]2[C:7](=[O:27])[NH:6][C:5]([NH2:4])=[N:13][C:12]1=2)[CH2:22][OH:23]

Participants

3

Reactant 1

HCID 135427290Acetamide,N-(9-((2-(acetyloxy)-1-((acetyloxy)methyl)ethoxy)methyl)-6,9-dihydro-6-oxo-1H-purin-2-yl)-

Product 1

HCID 135398740Ganciclovir

Reagents, catalysts & solvents 1

HCID 6329MethylamineSolvent

Procedure

A solution of 838 mg (2.2 mmole) of 2-acetamido-9-(1,3-diacetoxy-2-propoxymethyl)hypoxanthine in 8.5 ml of 40% methylamine (aqueous) was stirred at gentle reflux under N2 for 1 hour. The solution was then cooled and concentrated to dryness. The residual white solid was recrystallized from a minimum volume of H2O containing 2 drops of acetic acid. After standing in the refrigerator, the product was collected on a filter and washed with a small amount of H2O, then acetone. The material was dried under high vacuum at 75° for 3 hours to giive 529 mg (90% based on hydration with 0.75H2O) of white crystals, mp 249°-250° dec. The material was homogeneous by TLC (80:20:2 CHCl3 --MeOH--H2O), and the structure was confirmed by NMR.

Workup

  1. temperatureat gentle reflux under N2 for 1 hour
  2. temperatureThe solution was then cooled
  3. concentrationconcentrated to dryness
  4. customThe residual white solid was recrystallized from a minimum volume of H2O containing 2 drops of acetic acid
  5. customthe product was collected on
  6. filtrationa filter
  7. washwashed with a small amount of H2O
  8. customThe material was dried under high vacuum at 75° for 3 hours to giive 529 mg (90% based on hydration with 0.75H2O) of white crystals, mp 249°-250° dec

Sources & evidence

ORD record
ord-2dd1d1e472ca4b419cf4ca57a5fff363
Source dataset
uspto-grants-1989_03
Patent number
US04816447

Reaction notes

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