Potassium Carbonate → HCID 67054966, compound

Participants

Reaction Steps

A mixture of tert-butyl 4-[3-cyanoprop-2-en-1-yl]-3-(difluoromethyl)piperazine-1-carboxylate (0.12 g, 0.40 mmol from Step 5) and 4-(1H-pyrazol-4-yl)-7-{[2-(trimethylsilyl)ethoxy]methyl}-7H-pyrrolo[2,3-d]pyrimidine (0.12 g, 0.40 mmol, prepared as described in WO 2007/070514, Example 65) and potassium carbonate (0.16 g, 1.2 mmol) in DMF (0.36 mL) was stirred for 4.5 h. The mixture was then filtered, the filtrate was diluted with EtOAc, washed with water (thrice), brine, dried over sodium sulfate, decanted and concentrated. Flash chromatography on a 40 g silica gel cartridge eluting with a gradient of 0-80% solvent mixture [A] in hexanes ([A]=10% IPA: 50% EtOAc: 40% Hexanes) afforded a purified product (130 mg, 53%). 1H NMR (300 MHz, CDCl3): δ 8.83 (s, 2H), 8.33-8.28 (m, 4H), 7.42-7.38 (d, 2H), 6.79-6.76 (d, 2H), 5.89 (td, 1H), 5.63 (td, 1H), 5.67 (s, 4H), 4.57 (tt, 2H), 4.18-1.10 (m, 26H), 1.45, 1.43, 1.40 (3s, together 18H), 0.92 (dd, 4H), −0.08 (s, 18H); LCMS (M+H)+: 617.3.

Provenance & Evidence