Sodium Hydroxide → Penciclovir

HRID 1368675Notes

Reaction equation

HRID 1368675 reaction equation
[NH2:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[CH2:11][CH2:12][CH:13]2[CH2:18][O:17]C(C)(C)[O:15][CH2:14]2)=[C:4](Cl)[N:3]=1.[OH-:22].[Na+]>Cl>[OH:15][CH2:14][CH:13]([CH2:18][OH:17])[CH2:12][CH2:11][N:8]1[CH:7]=[N:6][C:5]2[C:4](=[O:22])[NH:3][C:2]([NH2:1])=[N:10][C:9]1=2

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 117713466-Chloro-9-[2-(2,2-dimethyl-1,3-dioxan-5-yl)ethyl]-9H-purin-2-amine

Product 1

HCID 135398748PenciclovirYield 72%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

2-Amino-6-chloro-9-[2-(2,2-dimethyl-1,3-dioxan-5-yl)-ethyl]purine (3.74 g, 12 mmol) in hydrochloric acid (2.0M, 12 ml) was heated under reflux for 1.5 hours. The solution was neutralised with aqueous sodium hydroxide (10%) and then allowed to cool. The solution was filtered and the solid washed with water to afford 9-(4-hydroxy-3-hydroxymethylbut-1-yl)guanine as a white crystalline solid (2.18 g, 72%), m.p. 275-277° C.; (Found: C, 47.31; H, 6.02; N, 27.81%; C10H15N5O3 requires C, 47.43; H, 5.97; N, 27.65%).

Workup

  1. temperatureunder reflux for 1.5 hours
  2. temperatureto cool
  3. filtrationThe solution was filtered
  4. washthe solid washed with water

Sources & evidence

ORD record
ord-561a498f7df3401189c50c38290d124c
Source dataset
uspto-grants-2003_06
Patent number
US06573378B1

Reaction notes

Loading…