Trimethylaluminum → HCID 59860337, compound

Participants

Reaction Conditions

Reaction Steps

Dissolve (S)-[1-(4-chloro-5-fluoropyrimidin-2-yl)-pyrrolidin-3-yl]-(2,4-dichlorobenzyl)-amine (318 mg, 0.84 mmol) in dry tetrahydrofuran (7.5 mL) and add trimethylaluminium (510 μL, 1.01 mmol, 2 M in hexanes) and tetrakis(triphenylphosphine)palladium(0) (68 mg, 0.06 mmol). Stir at 70° C. overnight. Quench by addition of water and extract with chloroform. Combine the organic layers and wash with saturated aqueous sodium chloride, dry (magnesium sulfate), filter and chromatograph on silica gel. Dissolve the residue in methanol (2 mL) and deposit onto SCX cartridge, eluting with methanol, then 2 M ammonia in methanol. Concentrate the ammonia washing to give the title compound (180 mg, 60%). 1H NMR (400 MHz, MeOH-d4) δ 7.88 (1H, d, J=6.4 Hz), 7.43-7.54 (2H, m), 7.27-7.37 (1H, m), 3.84-3.96 (4H, m), 3.67-3.78 (1H, m), 3.55-3.64 (1H, m), 3.43-3.53 (1H, m), 2.41 (3H, s), 2.14-2.26 (1H, m), 1.89-2.00 (1H, m); MS (ES): m/z=355 [M+].

Provenance & Evidence