Potassium Carbonate → HCID 67199869, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of (2,5-dichloro-8-methylquinolin-3-yl)methanol (500 mg, 2.06 mmol), o-tolylboronic acid (337 mg, 2.48 mmol) and K2CO3 (428 mg, 3.09 mmol) in DME (8 mL) and water (2 mL) was degassed for 5 minutes. Pd(PPh3)4 (119 mg, 0.1 mmol) was added and the reaction mixture was degassed for a further 5 minutes then heated to 120° C. under microwave irradiation for 1 h. The solvent was removed in vacuo and the residue was dissolved in DMF (30 mL). To this solution was added sodium hydride (60% in mineral oil, 102 mg, 4.27 mmol) and the mixture was stirred at r.t. for 30 minutes. 2-Amino-4-chloro-6-methylpyrimidine (490 mg, 3.41 mmol) was added and the mixture was stirred at r.t. for 18 h. The mixture was diluted with EtOAc (150 mL) and washed with water (7×30 mL). The organic layer was separated, dried (MgSO4) and the solvent removed in vacuo. Purification by column chromatography (SiO2, 0-5% MeOH in DCM) then by preparative HPLC (Method 1) gave the title compound as a white solid (100 mg, 12%). δH (CDCl3) 8.72 (s, 1H), 7.44-7.55 (m, 2H), 7.24-7.36 (m, 4H), 5.99 (s, 1H), 5.27 (s, 2H), 4.92 (br s, 2H), 2.73 (s, 3H), 2.24 (s, 3H), 2.18 (s, 3H). LCMS (ES+) 405.1, 407.0 (M+H)+, RT 2.91 minutes (Method 3).

Provenance & Evidence