Dimethylformamide → HCID 58180927, compound

Participants

Reaction Steps

A mixture of tert-butyl 4-[3-cyanoprop-2-en-1-yl]-3-(methoxymethyl)piperazine-1-carboxylate (54 mg, 0.18 mmol; as a mixture of E- and Z-olefin isomers from Step 2) and 4-(1H-pyrazol-4-yl)-7-{[2-(trimethylsilyl)ethoxy]methyl}-7H-pyrrolo[2,3-d]pyrimidine (58 mg, 0.18 mmol, prepared as described in WO 2007/070514 Example 65) in DMF (0.28 mL, 3.6 mmol) was treated with potassium carbonate (0.081 g, 0.58 mmol) and stirred for 5 h. The mixture was filtered and the filtrate was diluted with EtOAc, which was then washed with water (3 times), brine (once), dried over sodium sulfate, decanted and concentrated. Flash chromatography, using a 12 g silica gel cartridge and eluting with a gradient of 0-100% EtOAc in hexanes afforded an impure mixture of diastereomers which was used without further purification in the next step (91 mg, 57%). LCMS (M+H)+: 611.3.

Provenance & Evidence