Tributylvinyltin → HCID 86668114, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 2,4-dichloro-7-(4-fluorophenyl)-6,7-dihydro-5H-cyclopenta[d]pyrimidine (0.1 g, 0.353 mmol), tributylethenylstannane (0.118 g, 0.371 mmol), tetrakis(triphenylphosphine)palladium (0.0081 g, 0.0070 mmol) in toluene (20 mL) was refluxed at 110° C. for 2 h under nitrogen. The solvent was removed under reduced pressure (high vacuum) and the residue was dissolved in 4 mL of THF/MeOH (3:1). 2-(2-Aminoethoxy)-4-nitrobenzonitrile (0.088 g, 0.424 mmol) was added and the mixture was refluxed at 75° C. for 18 h while monitoring by LC-MS. The solvent was removed under reduced pressure and the residue was dissolved in dichloromethane (5 mL) and silica (1 g). The resultant slurry of the compound on silica was subjected to flash chromatography using a Teledyne Isco instrument (4 g RediSep silica column, 10% methanol in chloroform) to get 2-(2-((2-(2-chloro-7-(4-fluorophenyl)-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)ethyl)amino)ethoxy)-4-nitrobenzonitrile (0.035 g, 20.56%) as a dark brown gummy liquid. LC-MS (M+H)+=482.0. 1H NMR: (400 MHz, CDCl3) δ ppm 7.93 (1H, d, J=8.4 Hz), 7.87 (1H, s), 7.74 (1H, d, J=8.4 Hz), 7.13-7.10 (2H, m), 7.02-6.98 (2H, m), 4.45-4.44 (2H, m), 4.36 (1H, t, J=8.4 Hz), 3.44-3.41 (4H, m), 3.11-3.09 (2H, m), 2.97-2.88 (2H, m), 2.74-2.66 (1H, m), 2.21-2.12 (1H, m).

Provenance & Evidence