Hydrochloric Acid → HCID 136351945, compound

Participants

Reaction Steps

Sodium tert-butoxide (40.3 mg, 0.42 mmol) and methyl 2-oxo-5-indolinecarboxylate (17.6 mg, 0.092 mmol) in N-methylpyrrolidinone (1 mL) under nitrogen atmosphere were stirred for 5 min at room temperature. A solution of 4-chlorothieno[2,3-d]pyrimidine (0.1 mL, 0.84 M, corresponding to 14.3 mg, 0.084 mmol) in N-methylpyrrolidinone was added and the reaction mixture was stirred at room temperature over night. The reaction mixture was diluted with water (20 mL) and acidified with hydrochloric acid (1 M) and extracted with ethyl acetate (2×15 mL). The combined organic layer was washed with brine, dried with sodium sulphate, filtered and concentrated. The crude product was triturated with methylene chloride to give 10 mg (36% yield) of the title compound as a bronze solid. MS (AP−) m/z 324 (M−1).

Provenance & Evidence