Water → Penciclovir

HRID 1368674Notes

Reaction equation

HRID 1368674 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.[OH2:22]>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 962WaterHCID 117713466-Chloro-9-[2-(2,2-dimethyl-1,3-dioxan-5-yl)ethyl]-9H-purin-2-amine

Product 1

HCID 135398748PenciclovirYield 49%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

2-Amino-6-chloro-9-[2-(2,2-dimethyl-1,3-dioxan-5-yl)-ethyl]purine (0.59 g, 1.9 mmol) in hydrochloric acid (1.0M, 4 ml) was stirred at 60° C. for 24 hours. The solution was diluted with water and neutralised with Amberlite IR 45 (OH− form). The mixture was filtered, the resin washed with water and the solvent evaporated under reduced pressure. The residue was recrystallised from water to afford 9-(4-hydroxy-3-hydroxymethylbut-1-yl)guanine (238 mg, 49%), m.p. 275-277° C.; λmax (H2O) 253 (ε 11,500) and 270 (shoulder, ε 8,630) nm; νmax (KBr) 3420, 3140, 1690, 1645, and 1605 cm−1; δH [(CD3)2SO] 1.3-1.5 (3H, m, CHCH2CH2), 3.42 (4H, d, J 5 Hz, 2×CH2O), 3.99 (2H, t, J 7 Hz, CH2N), 4.41 (2H, br, D2O exchangeable, 2×OH), 6.44 (2H, s, D2O exchangeable, 2-NH2), 7.71 (1H, s, 8-H), and 10.55 (1H, br, D2O exchangeable, 1-H); (M+ found 253.1176. C10H15N5O3 requires M+ 253.1175).

Workup

  1. filtrationThe mixture was filtered
  2. washthe resin washed with water
  3. customthe solvent evaporated under reduced pressure
  4. customThe residue was recrystallised from water

Sources & evidence

ORD record
ord-52cb637f367e41e0af9214372cb393ae
Source dataset
uspto-grants-2003_06
Patent number
US06573378B1

Reaction notes

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