Triethylamine → HCID 67148233, compound

Participants

Reaction Steps

Methyl 3-(benzoyloxy)-10-bromo-4-oxo-4,6,7,8,9,10-hexahydropyrimido[1,2-a]azepine-2-carboxylate (1.0 eq.) was added to a solution of (1R)-1-phenylethylamine (2.2 eq.) and triethylamine (1 eq) dissolved in N,N-dimethylformamide. The mixture was stirred vigorously for 2 hours at room temperature and then at 50° C. for 30 minutes. The solvent was removed under reduced pressure and the title crude product (a mixture 1:1 of diastereoisomers) for use without further purification. In an alternative procedure (Step 5A), solid methyl 3-(benzoyloxy)-10-bromo-4-oxo-4,6,7,8,9,10-hexahydropyrimido[1,2-a]azepine-2-carboxylate (1.0 eq.) was added to a solution of (1R)-1-phenylethylamine (4.5 eq.) dissolved in a 7:3 methanol/water mixture at −30° C. The reaction was carried out over night, then the temperature was raised to room temperature and the solvent concentrated to obtain a white solid that was filtered off and discarded. The title compound (as a mixture 7:3 of diastereoisomers) was extracted in dichloromethane from the mother liquid for use in the next step without further purification.

Provenance & Evidence