Ammonia → Acyclovir

HRID 614929Notes

Reaction equation

HRID 614929 reaction equation
C([O:9][CH2:10][CH2:11][O:12][CH2:13][N:14]1[CH:22]=[N:21][C:20]2[C:19](=[O:23])[NH:18][C:17]([NH2:24])=[N:16][C:15]1=2)(=O)C1C=CC=CC=1.N>CO>[OH:9][CH2:10][CH2:11][O:12][CH2:13][N:14]1[CH:22]=[N:21][C:20]2[C:19](=[O:23])[NH:18][C:17]([NH2:24])=[N:16][C:15]1=2

Participants

4

Reactant 2

HCID 222AmmoniaHCID 135506856AC1Nanky

Product 1

HCID 135398513AcyclovirYield 78.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

9-(benzoyloxyethoxymethyl)guanine (0.58g) and methanol (80ml) saturated with ammonia were heated in a bomb at 80° C. for 16 hours. The reaction mixture was removed from the bomb and the solvent evaporated under reduced pressure. The residue was thoroughly washed with ether and then recrystallized from methanol to give 9-(2-hydroxyethoxymethyl)guanine (0.31g., 75% of theoretical), m.p. 256.5°-257° C.

Workup

  1. customThe reaction mixture was removed from the bomb
  2. customthe solvent evaporated under reduced pressure
  3. washThe residue was thoroughly washed with ether
  4. customrecrystallized from methanol

Sources & evidence

ORD record
ord-5ca4fc4429b2484da9cc3be34d6b1932
Source dataset
uspto-grants-1979_03
Patent number
US04146715

Reaction notes

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