Triphenylphosphine → HCID 89579814, compound

Participants

Reaction Conditions

Reaction Steps

8-(5-Bromothieno[2,3-d]pyrimidin-4-yl)-N-cyclobutyl-N-methyl-8-azabicyclo[3.2.1]octan-3-amine (82.5 mg, 0.20 mmol) in dimethoxyethane (4 mL) and 2 M sodium carbonate solution (1 mL) was treated with (2-methoxy-3-pyridyl)boronic acid (134 mg, 0.75 mmol) and palladium (II) acetate (12 mg, 0.053 mmol), triphenylphosphine (12 mg) and the reaction was stirred in a microwave at 85° C. over 1 h. The reaction was then diluted with ethyl acetate (25 mL) and saturated aqueous sodium bicarbonate solution (25 mL) and shaken. The ethyl acetate layer was then separated, dried over sodium sulphate and concentrated in vacuum to give a gum. The gum was dissolved in DMSO/water 1:1 (2.5 mL) and purified by reverse phase HPLC. The main peak was collected and concentrated in vacuum to give N-cyclobutyl-8-[5-(2-methoxy-3-pyridyl)thieno[2,3-d]pyrimidin-4-yl]-N-methyl-8-azabicyclo[3.2.1]octan-3-amine as a gum (32 mg, 0.073 mmol, 36%). LCMS RT=4.76 min. M+1=436. 1H NMR (CDCl3) δ: 1.1 (2H, t, J=12 Hz), 1.3-1.9 (1H, m), 1.9 (3H, s), 2.2 (1H, br m), 2.9 (1H, br m), 3.9 (3H, s), 4.3 (2H, br s), 7.0 (1H, q, J=6 Hz, J′=4 Hz), 7.25 (1H, s), 7.55 (1H, d, J=6 Hz), 8.2 (1H, d, J=4 Hz), 8.5 (1H, s).

Provenance & Evidence