Ammonia → HCID 58466239, compound

Participants

Reaction Conditions

Reaction Steps

Ammonia gas was bubbled through a solution of 4,4-difluoro-2′-(neopentyloxy)-7′-(pyrimidin-5-yl)spiro[pyrrolidine-2,9′-xanthene]-5-thione (0.013 g, 0.028 mmol) in THF (0.350 mL) at 55° C. for 2 minutes. Mercury(II) chloride (0.011 g, 0.042 mmol) was added in one portion and ammonia gas was bubbled through for 3 more minutes while heating at 55° C. (THF solution replenished as necessary to maintain a volume of ˜0.2-0.3 mL). The resulting reaction was stirred at 55° C. under nitrogen atmosphere for 14 hours. After cooling, the reaction was partitioned between CH2Cl2 (25 mL) and water (10 mL). The reaction mixture was diluted with a 10:1 mixture of saturated aqueous ammonium chloride/ammonium hydroxide, the layers were separated and the aqueous layer was extracted with CH2Cl2 (3×25 mL). The combined organic extracts were washed with a 10:1 mixture of saturated aqueous ammonium chloride/ammonium hydroxide, water, saturated aqueous sodium chloride, and dried over sodium sulfate. The solution was filtered and concentrated in vacuo to provide a residue that was purified by filtering through a pad of silica gel by eluting with 1:10 MeOH 2 M ammonia solution in CH2Cl2 followed by further purification by preparative thin layer chromatography (20:1 CHCl3/MeOH) to provide 4,4-difluoro-2′-(neopentyloxy)-7′-(pyrimidin-5-yl)-3,4-dihydrospiro[pyrrole-2,9′-xanthen]-5-amine as a white solid after triturating with pentane. MS m/z=451.2 [M+H]. This procedure is analogous to that described in Foloppe et al, Tetrahedron Letters, 33, 20, pp. 2803-2804, 1992.

Provenance & Evidence