Sulfuric Acid → HCID 11675422, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of (7-allyl-5,6-diphenyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-(tetrahydrothiophen-2-ylmethyl)-amine (Example 3, Step C, 0.20 mmol) in DMSO (1 mL) was added potassium tert-butoxide (50 mg, 0.45 mmol) and the solution was heated to 110° C. for 24 hours. The solution was then cooled, diluted with ethyl acetate, extracted with water (2×25 mL), dried and concentrated under reduced pressure. Acetone (1 mL) was then added, followed by sulfuric acid (1 N, aq., 1 mL) and mercury (II) chloride (250 mg, 1 mmol). The reaction mixture was heated to reflux for 4 hours, cooled, and purified by preparative HPLC (C8 column, water, acetonitrile, 0.1% TFA) to give the title compound. 1H-NMR (CDCl3): 1.95-1.39 (4 H, m), 2.78-2.57 (2 H, m), 3.75-3.42 (4 H, m), 5.91 (1 H, br s), 7.43-7.02 (10 H, m), 8.20 (1 H, s), 13.87 (1 H, br s). Mass Spectrum (ESI) m/e=387 (M+1).

Provenance & Evidence