HCID 13869780, compound → 6-Amino Didesacetyl Famciclovir

HRID 1461520Notes

Reaction equation

HRID 1461520 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]([NH2:21])[N:3]=1>C(O)(=O)C>[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]([CH2:18][OH:17])[CH2:14][OH:15])=[C:4]([NH2:21])[N:3]=1

Participants

3

Reactant 1

HCID 13869780HCID 13869780, compound

Product 1

HCID 138697816-Amino Didesacetyl FamciclovirYield 63%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 2,6-diamino-9-[2-(2,2-dimethyl-1,3-dioxan-5-yl)ethyl]purine (180 mg, 0.6 mmol) in 70% acetic acid (10 ml) was stirred for 1 hour at room temperature. The solvent was removed, the residue was suspended in methanol and sodium methoxide was added to neutralise. Column chromatography on silica gel eluting with chloroformmethanol mixtures (6:1, 4:1 and 3:1) gave 2,6-diamino-9-(4-hydroxy-3-hydroxymethylbut-1-yl)purine (95 mg, 63%), m.p. 187°-190° C.; λmax (H2O, pH6.5) 215 (ε25,500), 255 (ε7,290), and 280 (ε9,170) nm; νmax 3150, 1680, 1650, 1605, 1590, and 1410 cm-1 ; δH [(CD3)2SO] 1.46 (1 H, m, CHCH2CH2), 1.73 (2 H, q, J 7.1 Hz, CHCH2CH2), 3.3-3.5 (4 H, ddd (ABX), JAB 10.6 Hz, JAX 5.5 Hz and JBX 5.9 Hz, 2×CH2O), 4.01 (2 H, t, J 7.3 Hz, CH2N), 4.41 (2 H, br, D2O exchangeable, 2×OH), 5.70 (2 H, s, D2O exchangeable, NH2), 6.56 (2 H, s, D2O exchangeable, NH2), and 7.69 (1 H, s, 8-H) (Found: C, 46.09; H, 6.32; N, 31.69%; C10H16N6O2 0.1CHCl3 requires C, 45.91; H, 6.14; N, 31.81%).

Workup

  1. customThe solvent was removed
  2. additionsodium methoxide was added

Sources & evidence

ORD record
ord-0a855ca3640d498ab7ba40119acce7de
Source dataset
uspto-grants-1991_12
Patent number
US05075445

Reaction notes

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