Triethylamine → HCID 178470088, compound

Participants

Reaction Steps

To a stirred solution of ethyl 2-(1-(benzyloxycarbonylamino)-4-hydroxycyclohexyl)-5-hydroxy-1,6-dihydropyrimidine-4-carboxylate (1.75 g, 4.05 mmol) in THF (25 mL) was added methanesulfonyl chloride (0.94 mmol, 12.17 mmol) and triethylamine (1.7 mL, 12.75 mmol) at 5° C. and the mixture stirred at room temperature for 18 h. The resulting white precipitate was filtered off and washed with THF. The filtrate and washings were concentrated to afford an amber oil. A solution of this oil in methanol (20 mL) was treated with K2CO3 (560 mg, 4.05 mmol) at room temperature for 3 h. The mixture was then concentrated and the residue dissolved in ethyl acetate (200 mL), washed with 1N HCl (100 mL) followed by brine (100 mL) and then dried (Na2SO4), filtered and concentrated to give 2.3 g of the title compound as an amber oil, which was used in the next step without further purification. LCMS (M+H)=588.41.

Provenance & Evidence