HCID 58466268, compound → HCID 67382832, compound

Participants

Reaction Steps

Methyl magnesium chloride, 22 wt % in THF (5.0 mL, 14.88 mmol), was added to a solution of 2-(neopentyloxy)-7-(pyrimidin-5-yl)-9H-xanthen-9-one (2.2 g, 6.10 mmol) in THF (61.0 mL) at 0° C. After 2 hours, the reaction mixture was quenched with saturated aqueous ammonium chloride (200 mL) and extracted with EtOAc (3×200 mL). The combined organic extracts were washed with saturated aqueous ammonium chloride, water, saturated aqueous sodium chloride, and dried over sodium sulfate. The solution was filtered and concentrated in vacuo to afford 9-methyl-2-(neopentyloxy)-7-(pyrimidin-5-yl)-9H-xanthen-9-ol which used directly for the next reaction without further purification. Pyridinium p-toluene-sulfonate (0.140 g, 0.558 mmol) was added to a solution of 9-methyl-2-(neopentyloxy)-7-(pyrimidin-5-yl)-9H-xanthen-9-ol (0.200 g, 0.531 mmol) in DCE (2 mL) at 65° C. The reaction was monitored by and TLC analysis (1:1 Hex/EtOAc) and after 2 hours the solution was allowed to cool and was poured into saturated aqueous sodium bicarbonate (25 mL) and the layers were separated. The aqueous layer was extracted with CH2Cl2 (3×15 mL). The combined organic extracts were washed with saturated aqueous sodium chloride, and dried over sodium sulfate. The solution was filtered and concentrated in vacuo to give the crude material which was taken up in toluene and concentrated twice to remove residual pyridine. The product was used without further purification. MS m/z=359.2 [M+H].

Provenance & Evidence