Sodium Carbonate → (S)-4-(7-(3-(2-methylpyrrolidin-1-yl)phenylamino)thiazolo[5,4-d]pyrimidin-5-yl)benzamide

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The mixture of (S)-5-chloro-N-(3-methoxy-5-(2-methylpyrrolidin-1-yl)phenyl)thiazolo[5,4-d]pyrimidin-7-amine (100 mg, 0.29 mmol), 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide (77 mg, 0.29 mmol), Pd2(dba)3 (33 mg, 0.058 mmol), X-Phos (55 mg, 0.116 mmol) and Na2CO3 (123 mg, 1.16 mmol) in dioxane (20 mL) and water (5 mL) was heated to 100° C. with stirring for 16 h under N2. The solvent was removed in vacuo and the resulting residue was purified by column chromatography (DCM:MeOH=80:1) to afford (S)-4-(7-(3-(2-methylpyrrolidin-1-yl)phenylamino)thiazolo[5,4-d]pyrimidin-5-yl)benzamide (26 mg, 21%) as a yellow solid. 1H NMR (300 MHz, DMSO): δ 10.02 (s, 1H), 9.39 (s, 1H), 8.46-8.44 (m, 2H), 8.10 (s, 1H), 8.00-7.97 (m, 2H), 7.48-7.39 (m, 2H), 7.29-7.15 (m, 2H), 6.35 (d, 1H, J=7.8 Hz), 3.91 (brs, 1H), 3.41-3.31 (m, 1H), 3.19-3.16 (m, 1H), 2.08-1.98 (m, 2H), 1.71 (brs, 1H), 1.15 (d, 3H, J=6.3 Hz). LC-MS: 431 [M+H]+, tR=1.57 min. HPLC: 95.67% at 214 nm, 95.15% at 254 nm, tR=3.14 min.

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