Sodium Carbonate → 3-(4-Amino-2-chlorothieno[3,2-d]pyrimidin-7-yl)benzoic acid

Participants

Reaction Conditions

Reaction Steps

7-Bromo-2-chlorothieno[3,2-d]pyrimidin-4-amine (500 mg, 1.90 mmol) was dissolved in dioxane (10 mL) and 2.0 N sodium carbonate (2.85 mL, 5.70 mmol) and 3-boronobenzoic acid (316 mg, 1.90 mmol) were added. Nitrogen was flown to the mixture solution for 10 minutes and then Pd2(PPh3)Cl2 (80 mg, 0.11 mmol) and t-ButylXphos (73 mg, 0.17 mmol) were added. The reaction mixture solution was stirred at 90° C. for 6 hours and then filtered with celite. The organic layer was concentrated and then 2.0 N sodium hydroxide solution was added until the pH reached 10. After extracting with ethyl acetate, the aqueous layer was adjusted to pH 5 by adding 2.0 N hydrochloric acid solution. Thus prepared white solid was filtered and dried using nitrogen gas. The resultant target compound (380 mg, 65% yield) was used in the following reaction without purification.

Provenance & Evidence