Sodium Carbonate → tert-butyl(S)-2-(4-chlorophenyl)-3-(4-((R)-5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)piperazin-1-yl)-3-oxopropyl(isopropyl)carbamate

Participants

Reaction Steps

HBTU (0.469 g, 1.24 mmol) was added to a solution of (R)-5-methyl-4-(piperazin-1-yl)-6,7-dihydro-5H-cyclopenta[d]pyrimidine dihydrochloride (0.360 g, 1.24 mmol), (S)-3-(tert-butoxycarbonyl(isopropyl)amino)-2-(4-chlorophenyl)propanoic acid (0.423 g, 1.24 mmol), and DIEA (0.646 ml, 3.71 mmol) in DCM (8 mL). The reaction mixture was stirred at room temperature for 2 hours, after which 2M Na2CO3 was added. The reaction mixture was extracted with DCM, and the combined extracts were dried (Na2SO4), filtered, and concentrated. The crude was flashed on a Biotage 40S (ca. 175 mL 4:1 DCM:EA flushed to elute DIEA, then gradient to 1:4 DCM:EA) to give tert-butyl (S)-2-(4-chlorophenyl)-3-(4-((R)-5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)piperazin-1-yl)-3-oxopropyl(isopropyl)carbamate (0.679 g, 101% yield) as a pale yellow syrup. LC/MS (APCI+) m/z 542.1 [M+H]+.

Provenance & Evidence