Isopropanol → N-(4-methoxy-phenyl)-6-methyl-5H-pyrrolo[3,2-d]pyrimidine-2,4-diamine

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Reaction Steps

To a 100-mL round-bottomed flask, flushed with nitrogen, were added 10 (0.2 g, 0.7 mmol), 4-methoxy-phenylamine (0.12 g, 1.05 mmol), i-PrOH (20 mL), and 2-3 drops of concd HCl. The reaction mixture was heated at reflux with stirring for 45 min until the starting material 10 disappeared (TLC). The reaction solution was allowed to cool to room temperature; the solvent was removed under reduced pressure, 1,4-dioxane (10 mL) and 10 mL of 15% KOH aqueous solution were added. The resulting mixture was heated at reflux overnight. After cooling the reaction solution was neutralized with 1 N HCl, and then evaporated in vacuo to dryness and the residue was purified by column chromatography on silica gel with 2% MeOH in CHCl3 as the eluent. Fractions containing the product (TLC) were combined and evaporated to afford 0.1 g (53%) of AAG11 as a brown solid: mp 201-202° C.; Rf0.42 (MeOH/CHCl3, 1:5); 1H NMR (DMSO-d6) δ 2.34 (s, 3 H), 3.78 (s, 3 H), 5.33 (s, 2 H), 5.75 (s, 1 H), 6.86 (d, 2 H, J=6.3 Hz), 7.72 (d, 2 H, J=6.3 Hz), 8.45 (s, 1 H), 8.52 (s, 1 H). Anal. (C14H15N5O0.71CHCl30.81HCl) C, H, N.

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