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ChemicalBook CAS DataBase List Ganciclovir
82410-32-0

Ganciclovir synthesis

8synthesis methods
-

Yield:82410-32-0 87%

Reaction Conditions:

with acetic acid in water;methylamine

Steps:

8 Preparation of 9-(1,3-dihydroxy-2-propoxymethyl)guanine 12 and 7-(1,3-dihydroxy-2-propoxymethyl)guanine 11
Example 8 Preparation of 9-(1,3-dihydroxy-2-propoxymethyl)guanine 12 and 7-(1,3-dihydroxy-2-propoxymethyl)guanine 11 Compound 9 (8.0 g) was dissolved in 100 ml of aqueous methylamine (40%) and gently refluxed for 1.5 hours, and then was evaporated to dryness to give a white solid. The solid was crystallized from 50 ml of water and 10 drops of acetic acid (to neutralize amine and remove the color) to give a white crystalline product 12 (4.63 g, 87%). mp>300° (dec.); Rf 0.62 (CH3 OH:CHCl3 =1:1); UV (H2 O) pH7 λmax 251.5 (ε 10180), 272.0 (sh, ε 7500), pH2 λmax 253.5 (ε9840), pH 11 λmax 265.6 (ε 8060); 1 H NMR (DMSO-d6) δ 10.64 (s, 1H, AcNH, D2 O exchangeable), 7.80 (s, 1H, 8-H), 6.49 (s, 2H, NH2 D2 O exchangeable), 5.43 (s, 2H, 1'-H), 4.61 (t, 2H, OH, D2 O exchangeable), 3.55-3.28 (m, 5H, 4'-H, 5'-H, 3'-H).

References:

University of Georgia Research Foundation, Inc. US5583225, 1996, A

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