Ammonia → Acyclovir

HRID 614927Notes

Reaction equation

HRID 614927 reaction equation
Cl[C:2]1[NH:3][C:4](=[O:16])[C:5]2[N:6]=[CH:7][N:8]([CH2:11][O:12][CH2:13][CH2:14][OH:15])[C:9]=2[N:10]=1.[NH3:17]>CO>[OH:15][CH2:14][CH2:13][O:12][CH2:11][N:8]1[CH:7]=[N:6][C:5]2[C:4](=[O:16])[NH:3][C:2]([NH2:17])=[N:10][C:9]1=2

Participants

4

Reactant 2

HCID 222AmmoniaHCID 1356751292-Chloro-9-(2-hydroxyethoxymethyl)hypoxanthine

Product 1

HCID 135398513Acyclovir

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
125 °C

Procedure

A mixture of 2-chloro-9-(2-hydroxyethoxymethyl) hypoxanthine (0.375g) and methanol (80ml) saturated with anhydrous ammonia was heated in a bomb at 125° C. for 5 hours. The bomb was cooled in an ice bath and the reaction mixture removed. Solvent and excess ammonia were removed under reduced pressure at 50° C. After the residue was triturated with cold water to remove the ammonium chloride formed, the remaining solid was dried and then recrystallized from methanol to give pure 9-(2-hydroxyethoxymethyl)guanine (0.24g), m.p. 256.5°-257° C.

Workup

  1. temperatureThe bomb was cooled in an ice bath
  2. customthe reaction mixture removed
  3. customSolvent and excess ammonia were removed under reduced pressure at 50° C
  4. customAfter the residue was triturated with cold water
  5. customto remove the ammonium chloride
  6. customformed
  7. customthe remaining solid was dried
  8. customrecrystallized from methanol

Sources & evidence

ORD record
ord-a66fb11b054f44cc9e70c895cd0e47d5
Source dataset
uspto-grants-1979_03
Patent number
US04146715

Reaction notes

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