Sodium bis(trimethylsilyl)amide → HCID 56949508, compound

Participants

Reaction Steps

2-[(4-chloro-6-{[(2,4-dimethyl-1,3-thiazol-5-yl)methyl]amino}-5-methylpyrimidin-2-yl)oxy]ethanol G1 (17 mg, 0.052 mmol) and 2-bromo-1,8-naphthyridine (11 mg, 0.053 mmol) were placed in a test tube and dissolved in THF (1 mL). A 2 M solution of NaHMDS in THF (39 μL, 0.078 mmol) was added at ambient temperature, and the reaction was stirred overnight. Solvent was then removed, and the product was purified by silica gel flash column chromatography (EtOAc/hexanes gradient). 10 mg (42%) of G2 were isolated as an off-white solid. 1H NMR (499 MHz, DMSO-d6): δ 8.97 (s, 1H); 8.56 (d, J=8.03 Hz, 1H); 8.44 (d, J=8.81 Hz, 1H); 7.89-7.84 (m, 1H); 7.62 (dd, J=7.95, 4.62 Hz, 1H); 7.26 (d, J=8.79 Hz, 1H); 4.78 (d, J=5.18 Hz, 2H); 4.66 (d, J=4.97 Hz, 2H); 4.57 (d, J=5.78 Hz, 2H); 2.47 (s, 3H); 2.30 (s, 3H); 2.01 (s, 3H). HRMS (Electrospray): m/z 457.1206 (MH+).

Provenance & Evidence