Triethylamine → HCID 136085209, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of methyl 2-{(4S)-1-[(tert-butoxycarbonyl)(ethyl)amino]-5-hydroxy-4-methoxypentyl}-5-hydroxy-6-oxo-1,6-dihydropyrimidine-4-carboxylate (48 g, 112 mmol) in MeOH (1118 mL) was added 4-fluoro-benzylamine (28 g, 224 mmol) and triethylamine (31.2 mL, 224 mmol). The resulting mixture was sealed and heated at 80° C. overnight. The reaction mixture was cooled to ambient temperature, diluted with 10% citric acid (˜100 mL), and extracted with DCM (3×). The combined organic layers were dried over Na2SO4, filtered, and concentrated in vacuo. The crude residue was dissolved in acetonitrile and concentrated under reduced pressure (3×) to remove MeOH. The residue was dried under high vacuum for 2 days and used in the next reaction without purification. LC-MS: 523.5 (M+1).

Provenance & Evidence