Methane → Iso Ganciclovir

HRID 1194795Notes

Reaction equation

HRID 1194795 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][CH2:16][CH:17]([O:23]C(=O)C)[CH2:18][O:19]C(=O)C)[C:12]=2[N:13]=1)(=O)C.C(Cl)(Cl)Cl.CO.C>CN.O>[OH:23][CH:17]([CH2:18][OH:19])[CH2:16][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

Participants

7

Reactant 4

HCID 297MethaneHCID 887MethanolHCID 6212ChloroformHCID 135738512HCID 135738512, compound

Product 1

HCID 135446919Iso GanciclovirYield 89.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6329MethylamineSolvent

Procedure

A solution of 1.14 g (3.0 mmole) of 2-acetamide-9-(2,3-diacetoxy-1-propoxymethyl)hypoxanthine (VIII) from Step B above was heated at reflux in 40% aqueous methylamine with stirring under N2 for 1 hour and then cooled. TLC (80:20:2 CHCl3 --CH3OH--H2O) showed complete conversion to the title compound (I). The light orange solution was treated with some charcoal and filtered through Super-Cel. Concentration of the filtrate gave a solid which was recrystallized from H2O (adjusted to about pH 6 with a few drops of CH3COOH) to yield 687 mg of cream-colored crystals, mp 246°-247° dec.

Workup

  1. temperaturecooled
  2. filtrationfiltered through Super-Cel
  3. customConcentration of the filtrate gave a solid which
  4. customwas recrystallized from H2O (adjusted to about pH 6 with a few drops of CH3COOH)

Sources & evidence

ORD record
ord-096886c145554d4697b9551ccfcaefd8
Source dataset
uspto-grants-1989_03
Patent number
US04816447

Reaction notes

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