Cesium carbonate → HCID 67406947, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 40.0 mg (0.118 mmol) 2-(3-hydroxyphenyl)-5-[(4-methoxybenzyl)oxy]-3-methylpyrimidin-4(3H)-one in 1 ml NMP was added 27.6 mg (0.118 mmol) 4-iodoanisole, 46.2 mg (0.142 mmol) Cs2CO3, 2.18 μl (0.012 mmol) 2,2,6,6-tetramethyl-3,5-heptanedione, and 5.85 mg (0.059 mmol) copper(I) iodide. The reaction mixture was heated to 180° C. for 30 min in microwave, diluted with 2 ml water, 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 10.0 mg (26% yield) of 5-hydroxy-2-[3-(4-methoxyphenoxy)phenyl]-3-methylpyrimidin-4(3H)-one. 1H NMR δ (ppm) (DMSO-d6): 7.50 (1H, s), 7.45 (1H, t, J=7.93 Hz), 7.25 (1H, d, J=7.66 Hz), 7.09-7.02 (4H, m), 6.98 (2H, d, J=8.74 Hz), 3.75 (3H, s), 2.54 (3H, s). HRMS (ESI positive) calc M+H=325.1181 found 325.11.

Provenance & Evidence