Triethylsilane → HCID 178429378, compound

Participants

Reaction Steps

7-(Trans-3-((6-fluorobenzo[d]thiazol-2-yl)amino)cyclobutyl)-5,5-dimethyl-2-(methylthio)-5H-pyrrolo[2,3-d]pyrimidin-6(7H)-one (EXAMPLE 156) (0.200 g, 0.466 mmol) was dissolved in dry tetrahydrofuran (10 mL) under nitrogen. Palladium (10 wt. % on activated carbon, 0.080 g, 0.075 mmol) was added followed by triethylsilane (0.200 ml, 1.252 mmol). The suspension was stirred at room temperature. After 40 minutes additional triethylsilane (0.5 mL) was added and the reaction stirred for another 4 hours. Additional palladium/carbon (0.122 g) and triethylsilane (0.25 mL) were added and the reaction stirred for another 55 minutes. The mixture was filtered through a pad of CELITE® and evaporated to dryness under reduced pressure. Purification using silica chromatography (0-5% methanol in dichloromethane gradient) gave 7-(trans-3-((6-fluorobenzo[d]thiazol-2-yl)amino)cyclobutyl)-5,5-dimethyl-5H-pyrrolo[2,3-d]pyrimidin-6(7H)-one (0.091 g, 0.237 mmol, 51.0% yield) as a white solid. m/z: 384.0 (M+1); 1H NMR (400 MHz, CHLOROFORM-d) δ: ppm 1.42 (s, 6H) 2.42-2.53 (m, 2 H) 3.38-3.53 (m, 2 H) 4.55-4.65 (m, 1 H) 5.15-5.27 (m, 1 H) 7.03 (td, J=9.0 Hz, 2.6 Hz, 1H) 7.32 (dd, J=8.2 Hz, 2.6 Hz, 1H) 7.49 (dd, J=8.9 Hz, 4.7 Hz, 1H) 8.33 (s, 1H) 8.84 (s, 1H).

Provenance & Evidence