Ammonia → Acyclovir

HRID 2050014Notes

Reaction equation

HRID 2050014 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 (0.58 g) and methanol (80 ml) 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 (0.31 g., 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-154179e80b6947918072cf1fcd67eaa8
Source dataset
uspto-grants-1980_04
Patent number
US04199574

Reaction notes

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