Cesium carbonate → HCID 67426818, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 50.0 mg (0.106 mmol) 3-{5-[(4-methoxybenzyl)oxy]-1-methyl-6-oxo-1,6-dihydropyrimidin-2-yl}phenyl trifluoromethanesulfonate in 2 ml THF was added 7.8 mg (0.011 mmol) 1,1′-bis(diphenylphosphino)ferrocene-palladium(II)dichloride dichloromethane adduct, 18.3 mg (0.106 mmol) isoquinoline-5-boronic acid, and 300 μl (0.300 mmol) 1 M Cs2CO3. The reaction mixture was heated to 120° C. for 20 min in the microwave, then extracted with 10 ml EtOAc, and concentrated in vacuo. The oil was dissolved in 1 ml CH2Cl2, 1 ml TFA was added, and then concentrated in vacuo. Purification by mass-guided high throughput purification gave 15 mg (43% yield) of 2-(3-isoquinolin-5-ylphenyl)-5-hydroxy-3-methylpyrimidin-4(3H)-one. 1H NMR δ (ppm)(DMSO-d6): 9.62 (1 H, s), 8.58 (1 H, s), 8.34 (1 H, d, J=8.04 Hz), 7.97-7.86 (3 H, m), 7.74-7.66 (4 H, m), 7.57 (1 H, s), 2.54 (3 H, s). HRMS (ESI positive) tale (M+H)+=330.1237. Found 330.1237.

Provenance & Evidence