Sodium Carbonate → 4-(7-(3,4-dimethoxyphenylamino)thiazolo[5,4-d]pyrimidin-5-yl)-N-(2-(1-methyl-2-oxo-1,2-dihydropyridin-4-yl)ethyl)benzamide

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Reaction Steps

Under N2 atmosphere, 5-chloro-N-(3,4-dimethoxyphenyl)thiazolo[5,4-d]pyrimidin-7-amine (150 mg, 0.47 mmol), N-(2-(1-methyl-2-oxo-1,2-dihydropyridin-4-yl)ethyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide (220 mg, crude), Pd(PPh3)4 (40 mg, 0.035 mmol) and Na2CO3 (100 mg, 0.94 mmol) in 3 mL of water was added in 30 mL of 1,4-dioxane. The mixture was stirred at reflux for 18 hours. The solvent was removed under reduce pressure and the residue was purified by silica gel chromatography, eluting with DCM/MeOH (20/1, v/v) to give 4-(7-(3,4-dimethoxyphenylamino)thiazolo[5,4-d]pyrimidin-5-yl)-N-(2-(1-methyl-2-oxo-1,2-dihydropyridin-4-yl)ethyl)benzamide (30 mg, 12%) as a yellow sold. 1H NMR (300 MHz, CD3OD): δ 9.13 (s, 1H), 8.52-8.50 (m, 2H), 7.89-7.80 (m, 3H), 7.58 (d, 1H, J=6.9 Hz), 7.40 (dd, 1H, J1=8.4 Hz, J2=2.4 Hz), 7.03 (d, 1H, J=8.7 Hz), 6.46 (s, 1H), 6.38 (dd, 1H, J1=6.6 Hz, J2=1.8 Hz), 3.94 (s, 3H), 3.88 (s, 3H), 3.66 (t, 2H, J=7.0 Hz), 3.54 (s, 3H), 2.84 (t, 2H, J=7.0 Hz). LC-MS: 543 [M+H]+, 541 [M−H]−, tR=1.37 min. HPLC: 100% at 214 nm, 100% at 254 nm, tR=5.36 min.

Provenance & Evidence