Water → 2-Ethoxy-2-{[1-(2-methoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-yl]thio}-N-(4-methyl-1,3-thiazol-2-yl)acetamide

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Reaction Steps

Sodium hydride (95%, 3.7 mg, 0.15 mmol) was added to a stirred solution of 2-amino-4-methylthiazol (17.6 mg, 0.154 mmol) in anhydrous THF (4 mL). The reaction mixture was kept at ambient temperature for 5 minutes before ethyl ethoxy{[1-(2-methoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-yl]thio}acetate (50 mg, 0.129 mmol) was added. The reaction mixture was stirred at ambient temperature for 1 h. Water and DCM were added and the two phases were separated. The organic phase was dried over MgSO4 and concentrated in vacuo. The residue was purified with column chromatography (silica gel, eluting with a gradient consisting of 40-100% EtOAc in heptane) to give the title compound as a colourless oil (1.1 mg), 1H NMR (300 MHz, CDCl3) δ 10.03 (br s, 1H), 8.74 (s, 1H), 8.26 (s, 1H), 7.47 (m, 2H), 7.12 (m, 2H), 6.91 (s, 1H), 6.58 (s, 1H), 4.02 (m, 1H), 3.81 (m, 4H), 2.38 (s, 3H), 1.34 (t, 3H), HRMS: calcd for (M+H+) C20H21N6O3S2: 457.1116. Found: 457.1116.

Provenance & Evidence