Electric Literature of 2468-56-6,Some common heterocyclic compound, 2468-56-6, name is 6-Iodohex-1-yne, molecular formula is C6H9I, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.
General procedure: Concentrated sulfuric acid (0.15 mL) was added under stirring at ambient temperature to a suspension of 25 mmole of uracil 3 or uracil derivatives, namely 6-methyluracil 4, thymine 5, quinazoline-2,4(1H,3H)-dione 6 and hexamethyldisilazane (HMDS, 62.5 mmol) in 100 mL of toluene. The mixture was refluxed for 4 h, the solvent and excessive HMDS were removed to afford bis(trimethylsilyl) ether derivative 7. This crude product was engaged in the next step without any previous purification. A solution of 40 mmole of appropriate alkyne (propargyl bromide, 5-iodo-1-pentyne, 6-iodo-1-hexyne) in DMF (3 mL) was added to the crude product 7 and the reaction mixture was stirred at 115-130 C for 12 h. After the solvent was distilled off under reduced pressure, 200 ml of chloroform was added to the residue, and the mixture was filtered. The filtrate was concentrated, and the residue was purified by column chromatography on silica gel using as eluent first petroleum ether, then petroleum ether-ethyl acetate (1.5:1) and then ethyl acetate. From the third fraction the target N1-alkynyl-3,4-dihydro-2,4-dioxopyrimidines (3a,b, 4b,c, 5a,b, 6a,b) were isolated.
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 6-Iodohex-1-yne, its application will become more common.