Sodium Carbonate → HCID 66599854, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (41.5 mg, 0.199 mmol) (Aldrich), 4-(5-chloro-2-(6-methoxypyridin-3-ylamino)pyridin-3-yl)-N,N-bis(4-methoxybenzyl)-6-methyl-1,3,5-triazin-2-amine (97 mg, 0.166 mmol), Pd2dba3 (6.08 mg, 6.64 μmol) (Strem Chemicals), and 2-(dicyclohexylphosphino)-2′,4′,6′,-tri-i-propyl-1,1′-biphenyl (6.33 mg, 0.013 mmol) (Strem Chemicals) was purged with argon, treated with dioxane (2 mL) and 1 M aqueous sodium carbonate (0.415 mL, 0.415 mmol), and heated in a microwave at 140° C. for 30 min. The reaction mixture was treated with 1 N NaOH and extracted with EtOAc (30 mL), washed with brine and dried over MgSO4, filtered and concentrated to give N,N-bis(4-methoxybenzyl)-4-(2-(6-methoxypyridin-3-ylamino)-5-(1-methyl-1H-pyrazol-4-yl)pyridin-3-yl)-6-methyl-1,3,5-triazin-2-amine (140 mg, 0.222 mmol) which was used in the next step without further purification. m/z (ESI, +ve ion) 630.0 (M+H)+. 1H NMR (400 MHz, CDCl3) δ 11.60 (1H, s); 8.83 (1H, d, J=2.5 Hz); 8.41 (1H, d, J=2.5 Hz); 8.27 (1H, d, J=2.7 Hz); 7.89 (1H, dd, J=8.8, 2.7 Hz); 7.68 (1H, s); 7.52 (1H, s); 7.21 (4H, dd, J=13.5, 8.6 Hz); 6.86 (4H, dd, J=13.1, 8.6 Hz); 6.71 (1H, d, J=9.0 Hz); 4.88 (2H, s); 4.82 (2H, s); 3.93 (3H, s); 3.93 (3H, s); 3.81 (3H, s); 3.78 (3H, s); 2.59 (3H, s).

Provenance & Evidence