Sodium Carbonate → (S)-1-(4-(4-chloro-6-(3-methylmorpholino)-1,3,5-triazin-2-yl)phenyl)-3-methylurea

Participants

Reaction Conditions

Reaction Steps

A mixture of (S)-4-(4,6-dichloro-1,3,5-triazin-2-yl)-3-methylmorpholine (step (i) example 1) (4 g, 16.1 mmol), 1-methyl-3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)urea (4.67 g, 16.1 mmol), bis(triphenylphosphene)palladium(II) dichloride (0.66 g, 0.8 mmol) and 2M Na2CO3 (8 ml, 19.6 mmol) in DME (32 ml) was heated in the microwave at 90° C. for 90 minutes. The mixture was diluted with DCM (200 mL), washed with water (200 mL), the organic layer passed through a PTFE hydrophobic frit and the solvent removed in vacuo to yield a black oil. The oil was purified by flash chromatography using Pet ether, EtOAc 0-100% gradient to yield an off-white solid of (S)-1-(4-(4-chloro-6-(3-methylmorpholino)-1,3,5-triazin-2-yl)phenyl)-3-methylurea. (932 mg, 15%)

Provenance & Evidence