Potassium Carbonate → HCID 18507388, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 250 mg (1.02 mmol) 2-amino-4-bromo-6-methylsulfanyl-pyrimidine-5-carbonitrile in 10 ml toluene at room temperature were added 310 mg (2.04 mmol) 2-methoxybenzeneboronic acid, 118 mg (0.10 mmol) tetrakis(triphenylphosphine) palladium(O) and 262 mg (2.04 mmol) potassium carbonate. The reaction mixture was heated at 100° C. for 16 h, then cooled to room temperature and partitioned between ethyl acetate and water. The phases were separated and the organic phase dried over sodium sulfate and concentrated in vacuo. Chromatography (ethyl acetate/hexane 1/4 then ethyl acetate/hexane 1/2) followed by trituration in hexane afforded 80 mg (29%) 2-amino-4-(2-methoxy-phenyl)-6-methylsulfanyl-pyrimidine-5-carbonitrile as a white crystalline solid. EI-MS m/e (%): 272 (M+, 32), 257 ([M—CH3]+, 100), 241 (17).

Provenance & Evidence