2-(Tributylstannyl)pyrimidine → HCID 71294030, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 3-((5R,7S)-5-(4-cyano-2-fluorophenyl)-7-hydroxy-6,7-dihydro-5H-pyrrolo[1,2-c]imidazol-7-yl)phenyl trifluoromethanesulfonate (20 mg, 0.043 mmol), 2-tributylstannanyl-pyrimidine (47.4 mg, 0.128 mmol) and palladium tetrakis (9.89 mg, 8.56 μmol) in toluene (400 μL) was allowed to stir at 100° C. for overnight. The crude was cooled and concentrated. The crude was partitioned between water and CH2Cl2. The aq. layer was extracted with EtOAc. The organic layer was washed with brine, dried over MgSO4, filtered, and concentrated. The crude was filtered through a plug of silica using EtOAc/heptane. Part of the residue was then purified via HPLC, using 10-90% MeCN/H2O to give 2 mg of the entitled product. MS 398.1 (M+H); LCMS condition B, retention time 0.95 min. 1H NMR (400 MHz, CDCl3) δ ppm 3.06 (dd, 1H), 3.41 (dd, 1H), 5.76-5.90 (m, 1H), 7.04 (s, 1H), 7.14 (t, 1H), 7.28 (t, 1H), 7.34-7.43 (m, 2H), 7.46 (t, 1H), 7.62 (dd, 1H), 7.68 (s, 1H), 8.30-8.40 (m, 1H), 8.52 (t, 1H), 8.73 (d, 2H).

Provenance & Evidence