Triethylamine → HCID 11440041, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 4-chloro-2-methylthio-5-pyrimidinecarboxylate (900 mg, 3.87 mmol) (Aldrich) and triethylamine (1.1 mL, 870 mg, 7.74 mmol) (Aldrich) in dioxane (50 mL) was treated with (±)-trans-3-(tert-butyl-dimethyl-silanyloxy)-cyclopentylamine (840 mg, 3.87 mmol) (from Example 9c supra). The mixture was stirred at reflux for 1 hour, then cooled and partitioned between brine and ethyl acetate. The organic layer was collected, dried over sodium sulfate, filtered and concentrated to a residue that was purified by silica gel column chromatography using a 0–20% ethyl acetate in hexanes gradient. The product isolated from this purification was then dissolved in anhydrous tetrahydrofuran (80 mL) and the resulting solution was cooled to 0° C. Followed addition in-portions of lithium aluminum hydride (440 mg, 11.61 mmol) (Aldrich) and the resulting mixture was allowed to warm to room temperature. After overnight stirring the reaction mixture was poured slowly into a vigorously stirred mixture of ethyl acetate and saturated aqueous potassium sodium tartrate solution. The organic layer was collected, dried over sodium sulfate, filtered and concentrated to an off white solid. This intermediate was then dissolved in dichloromethane (80 mL) and the resulting solution was treated with manganese dioxide (3.36 g, 38.70 mmol) (Aldrich). After overnight stirring the solids were filtered off, washed with tetrahydrofuran (approximately 30 mL) and the combined organic layer was concentrated to a residue that upon a silica gel column purification with 0–50% diethyl ether in hexanes gradient gave (±)-4-[trans-3-(tert-butyl-dimethyl-silanyloxy)-cyclopentylamino]-2-methylsulfanyl-pyrimidine-5-carbaldehyde as a viscous colorless oil. (Yield 888 mg, 62%).

Provenance & Evidence