Potassium Carbonate → 2-Butoxy-9-(3-hydroxypropyl)-8-methoxyadenine

Participants

Reaction Conditions

Reaction Steps

To a suspension of 2-butoxy-8-methoxy-9H-purin-6-amine trifluoroacetate (described in EP 1 728 793, Example 2-1, step (vi)) (20.0 g, 56.9 mmol) in NMP (111 g) was added water (1.7 g) and K2CO3 (23.61 g, 170.8 mmol). To the mixture 1-acetoxy-3-bromopropane (12.4 g, 68.3 mmol) was added and the mixture stirred at 30° C. for 3 hr. To the solution was added MeOH (79 g) and 2% aqueous NaOH (100 g) and stirred at 70° C. for 3 hr. After adding water (200 g) and cooling to 7° C., the suspension was filtered and the collected solid dried to give the subtitle compound as white solid. Yield 13.0 g, 78%; 1H NMR (DMSO-d6) δ 6.77 (bs, 2H), 4.57 (t, 1H), 4.16 (t, 2H), 4.04 (s, 3H), 3.89 (t, 2H), 3.42-3.38 (m, 2H), 1.85-1.78 (m, 2H), 1.68-1.61 (m, 2H), 1.41-1.35 (m, 2H), 0.92 (t, 3H)

Provenance & Evidence