Iodoethane → 6-(6-ethoxy-2-methyl-5-nitro-pyrimidin-4-yl)-2-methyl-5,6,7,8-tetrahydro-4H-thiazolo[4,5-d]azepine

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Reaction Steps

A suspension of 0.120 g (0.373 mmol) of 2-methyl-6-(2-methyl-4,5,7,8-tetrahydro-thiazolo[4,5-d]azepin-6-yl)-5-nitro-3H-pyrimidin-4-one (example 1), of 0.070 g (0.45 mmol) of the ethyl iodide and of 0.077 g (0.56 mmol) of potassium carbonate in 1.0 ml of N,N-dimethylformamide was stirred at room temperature for 4 hours. The reaction mixture was then poured into 50 ml of an ice/water mixture and extracted 3 times with 50 ml of ethylacetate. The combined ethylacetate phases were dried over magnesium sulfate and evaporated under reduced pressure. The residue formed was then chromatographed on silica gel using a 95:5 v/v mixture of dichloromethane and methanol as eluent giving in a first fraction 0.025 g (0.072 mmol, yield 19%) of the 6-(6-ethoxy-2-methyl-5-nitro-pyrimidin-4-yl)-2-methyl-5,6,7,8-tetrahydro-4H-thiazolo[4,5-d]azepine as yellow amorphous solid; MS: [M+H]+=350.

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