Silanamine, 1,1,1-trimethyl-N-(trimethylsilyl)-, potassium salt → HCID 178453660, compound

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Reaction Steps

To a solution of 2,4-dichloro-5-iodo-7-{[2-(trimethylsilyl)ethoxy]methyl}-7H-pyrrolo[2,3-d]pyrimidine (416 mg, 0.94 mmol), as prepared in Example 5, step 1, in THF (10 mL) was added tert-butyl(trans-3-hydroxycyclobutyl)methylcarbamate (175 mg, 0.94 mmol) and potassium hexamethyldisilazane (560 mg, 2.8 mmol, 3.0 mol eq) and the reaction was stirred at ambient temperature for 20 hrs. The reaction was then quenched with brine (3 mL) and stirred for 10 min, and diluted with ethyl acetate (60 mL) and water (10 mL). The organic layer was separated, washed with brine (10 mL), dried over Na2SO4, filtered and evaporated to give an oil which was purified via flash chromatography (eluting with a gradient of 0 iodobenzene diacetate 100% EtOAc in heptanes) to give the title compound (452 mg, 80% yield) as a colorless oil. 1H NMR (400 MHz, DMSO-d6) δ ppm 7.80 (s, 1H) 5.48 (s, 2H) 5.38 (t, J=6.54 Hz, 1H) 4.86 (br. s., 1H) 3.44-3.59 (m, 2H) 2.81 (s, 3H) 2.61-2.74 (m, 2H) 2.27-2.43 (m, 2H) 1.40 (s, 9H) 0.71-0.97 (m, 2H) −0.08 (s, 9H). m/z (APCI+) for C22H34ClIN4O4Si 509.0 (M+H)+.

Provenance & Evidence