Acetyl chloride → HCID 135923795, compound

Participants

Reaction Steps

To a stirred suspension of N-{4-hydroxy-5H-pyrrolo[3,2-d]pyrimidin-7-yl}methyl-2-(2,2-dimethyl-1,3-dioxolan-4-yl)-3-(methylthio)propan-1-amine (0.1 g, 0.28 mmol) in methanol (7 ml) was added a solution of acetyl chloride (0.22 g, 2.8 mmol) in methanol (3 ml) and the solution stirred at ambient temperature for 2.5 hr. Amberlyst A-21 resin was added and the solution made neutral before being filtered free of resin and concentrated to a light yellow gum (0.072 g). This was dissolved in aqueous methanol (1:1) and preabsorbed onto silica for chromatography over silica. Gradient elution with DCM/MeOH/0.88 NH3 cocktails ranging from 9:1:0.1 through to 6:4:0.1 in composition furnished the title compound as a precipitate (free base) in the latter fractions. This was recovered by filtration and dried to give a colourless solid (0.026 g). 1H NMR (CD3OD+DCl) δ 7.93 (s, 1H), 7.42 (s, 1H), 3.94 (s, 2H), 3.82 (q, J=4.8 Hz 1H), 3.58 (m, 2H), 2.89 (m, 2H), 2.66 (dd J=13.2, 6.6 Hz, 1H), 2.55 (dd J=13.2, 7.5 Hz, 1H), 2.13 (s, 3H), 1.94 (m, 1H). 13C NMR (CD3OD+DCl) δ 156.6, 145.2, 143.4, 129.1, 119.7, 115.8, 75.0, 65.9, 50.0, 45.9, 41.5, 36.6, 16.3. HR-ESMS MH+ 313.1332 C13H21N4O3S requires MH+ 313.1334 Δ 0.6 ppm.

Provenance & Evidence