Toluene → HCID 131723109, compound

Participants

Reaction Steps

5 g of 5-bromouracil (26.18 mmole) available from Aldrich Chemical Co., 0.196 g of sodium iodide (1.31 mmole), and 35 mL of DMF were added to a 200 mL two-necked round bottomed flask. The mixture was stirred for 10 minutes. 5.065 g of potassium carbonate (36.65 mmole) was added to the mixture. Then 8.3687 g of 80% propargyl bromide available from Aldrich Chemical Co. in toluene was added dropwise over 1.5 hours. The mixture was stirred at room temperature for 16 hours to yield a milky solution. The solution was added to a separatory funnel with 200 mL of deionized water and extracted twice with 100 mL portions of 1,2-dichloromethane. The organic layers were combined and dried over magnesium sulfate. The mixture was filtered to remove any solids and evaporated under vacuum to obtain a low volume liquid. The liquid was placed on a Kugelrohr apparatus to remove any DMF in the liquid to yield 1N,3N-bis(2-propynyl)-5-bromouracil as a solid which was approximately 98% pure as determined by HPLC.

Provenance & Evidence