Sodium Carbonate → HCID 86603175, compound

Participants

Reaction Steps

A 100 mL vial was charged with compound 34.1 (125 mg, 100 mol %), 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester (86 mg, 120 mole %), and PdCl2(PPh3)2 (33 mg, 20 mol %). To this was added DMF/H2O (4:1, 1 mL) along with 2N Na2CO3 (0.3 mL). The vial was flushed with nitrogen, sealed, and subjected to microwave irradiation (10 minutes, 300 W, 100° C.). The contents were cooled and concentrated in vacuo. The resulting residue was purified by reverse phase HPLC (aqueous 0.1% CF3COOH/MeCN gradient) resulting in a 1:1 mixture of 1-{5-[2-(thieno[3,2-d]pyrimidin-4-ylamino)-ethyl]-thiazol-2-yl}-3-(3-trifluoromethyl-phenyl)-urea; compound with 3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester (compound 50.1) and the titled compound. This mixture was dissolved in 4N HCl/dioxane (2 mL), stirred at room temperature for 15 minutes, and concentrated in vacuo to provide exclusively the HCl salt of the titled compound as a yellow powder LCMS [M+H]+ m/z 546.1.

Provenance & Evidence