Potassium Phosphate, Tribasic → HCID 86663958, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 5-bromo-2-chloropyrimidine (6.80 g, 35.1 mmol) in DMF (40 mL) was added [5-[2-(ethylcarbamoylamino)-7-(2-pyridyl)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]boronic acid (10 g, 29.24 mmol) and aqueous solution of K3PO4 (9.3 g, 43.86 mmol). The reaction mixture was degassed by purging N2 for 15 min followed by addition of bis(triphenylphosphine)palladium (II) chloride (3.10 g, 4.4 mmol). The reaction mixture was again degassed for 10-15 min then heated up to 80° C. for 2 h. After completion of reaction (by TLC), solvent was evaporated under reduced pressure, 50 mL water added followed by extraction with EtOAc (3×200 mL). The combined organics were washed with brine, dried over anhydrous Na2SO4, filtered and evaporated under reduced pressure. The crude residue was purified over 60-120 M silica-gel by using 5% MeOH: DCM to obtain an off white solid compound that was triturated with ether (4.80 g). Further product was obtained by repeating the extraction (1.20 g) giving a combined total product yield of 6.0 g (50%). 1H NMR (DMSO-d6): δ 1.12 (t, J=7.20 Hz, 3H), 3.20 (m, 2H), 6.83 (br s, 1H), 7.46 (m, 1H), 8.0 (m, 1H), 8.17 (s, 1H), 8.40 (s, 1H), 8.50 (d, J=8.0 Hz, 1H), 8.82 (d, J=4.0 Hz, 1H), 9.35 (s, 2H) and 10.61 (br s, 1H). MS: 411.16 [M+H]+.

Provenance & Evidence