Imidazole → HCID 86621230, compound

Participants

Reaction Steps

To a suspension of 0.69 g (10.11 mmol) imidazole and 1.07 g (10.5 mmol) triethylamine in 9 ml methylene chloride was added dropwise at −5 to 0° C. within 15 minutes 0.49 g (3.22 mmol) phosphorous oxychloride. After 15 minutes at −5° C., the resulting suspension was treated with 1.00 g (2.15 mmol) 3-chloro-benzoic acid 4-azido-6-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2-methyl-tetrahydro-furo[3,4-d]-1,3-dioxol-4-ylmethyl ester followed by 1 ml methylene chloride. The suspension was allowed to warm to room temperature within 15 minutes and then stirred at room temperature for 69 hours. The suspension was cooled to 0° C. and treated at this temperature with 10 ml water. The suspension was allowed to warm to room temperature and the layers were separated. The aqueous layer was extracted with methylene chloride (2×5 ml). The combined organic layer was dried over MgSO4, filtered, concentrated in vacuo, and dried in vacuo (<10 mbar) at 25° C. for 22 hours to afford 1.07 g (96%) of 3-chlorobenzoic acid 4-azido-6-(4-imidazol-1-yl-2-oxo-2H-pyrimidin-1-yl)-2-methyl-tetrahydro-furo[3,4-d]-1,3-dioxol-4-ylmethyl ester as a beige foam.

Provenance & Evidence