Sodium Hydroxide → 3-(4-amino-2-(6-(4-ethylpiperazin-1-yl)pyridin-3-ylamino)thieno[3,2-d]pyrimidin-7-yl)-N-methylbenzamide

Participants

Reaction Conditions

Reaction Steps

3-(4-Amino-2-chlorothieno[3,2-d]pyrimidin-7-yl)-N-methylbenzamide (20 mg, 0.063 mmol) was dissolved in dioxane (1 mL) and then sodium hydroxide (13 mg, 0.31 mmol) and 6-(4-ethylpiperazin-1-yl)pyridin-3-amine (19 mg, 0.094 mmol) were added. After flowing nitrogen gas to the reaction mixture for 10 minutes, Pd2(dba)3 (4 mg, 0.004 mmol) and X-phos (1 mg, 0.12 mmol) were added. The reaction mixture was stirred at 120° C. for 2 hours and filtered with celite. The filtrate was diluted with ethyl acetate and then washed with brine. The organic layer was dried with magnesium sulfate, filtered with celite, and then concentrated. Purification by chromatography (5% methanol/dichloromethane) yielded the target compound (17 mg, 55% yield) of Example 1.

Provenance & Evidence