Ammonium Hydroxide → N-(4-chloro-6-methyl-5H-pyrrolo[3,2-d]pyrimidin-2-yl)-2,2-dimethylpropanamide

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Reaction Steps

To a 100-mL round-bottomed flask was added 9 (1.16 g, 4.67 mmol) suspended in 30 mL phosphorus oxychloride. The reaction mixture was heated at reflux with stirring in an anhydrous atmosphere for 3 h. The dark orange solution was allowed to cool to room temperature and concentrated in vacuo. Water (20 mL) was then added to the residue at 0° C. with vigorous stirring to give an exothermic reaction. Concentrated aqueous ammonium hydroxide was added to pH 5 to give a precipitate, which was collected by filtration, washed with water (3×5 mL), and dried in vacuo. The crude product was purified by silica gel column chromatography with 2% MeOH/CHCl3. Recrystallization from MeOH afforded 1.07 g (86%) of 10 as a white solid: TLC Rf0.35 (MeOH/CHCl3, 1:10); mp 162-163° C.; 1H NMR (DMSO-d6) δ 1.19 (s, 9 H), 2.47 (s, 3 H), 6.33 (s, 1 H), 9.85 (s, 1 H), 12.07 (s, 1 H) Anal. (C12H15ClN4O) C, H, N, Cl.

Provenance & Evidence