Potassium Carbonate → HCID 86696512, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of benzyl ((2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)cyclopropyl)methyl)carbamate (500 mg, 1.510 mmol), 2-chloro-5-fluoropyrimidine (45 mg, 0.340 mmol), potassium carbonate (100 mg, 0.724 mmol), and tetrakis(triphenylphosphine) palladium (0) (10 mg, 8.65 μmol) in dioxane (2 mL) and water (0.4 mL) was heated to 100° C. in a sealed vial for 16 h. The mixture was diluted with EtOAc and washed with sat'd sodium carbonate. The EtOAc layer was concentrated to an amber oil. The crude product was purified by silica gel chromatography using 0-30% EtOAc/hexane as the eluent to give benzyl ((2-(5-fluoropyrimidin-2-yl)cyclopropyl)methyl)carbamate as a colorless oil (220 mg, 42%). 1H NMR (400 MHz, CHLOROFORM-d) d 8.45-8.31 (m, 2H), 7.36-7.30 (m, 5H), 5.10 (s, 2H), 4.07 (br. s., 1H, NH), 3.39-3.15 (m, 2H), 2.19 (dt, J=8.5, 4.4 Hz, 1H), 1.78-1.62 (m, 1H), 1.31 (dt, J=8.7, 4.5 Hz, 1H), 1.09-0.95 (m, 1H). LCMS: M+1=302.2.

Provenance & Evidence