Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) → 2-(4-chlorophenyl)-1-(4-((S)-5-methyl-5,7-dihydrothieno[3,4-d]pyrimidin-4-yl)piperazin-1-yl)-3-(2-methylaziridin-1-yl)propan-1-one

Participants

Reaction Steps

HBTU (37 mg, 0.097 mmol) was added to a solution of the (S)-5-methyl-4-(piperazin-1-yl)-5,7-dihydrothieno[3,4-d]pyrimidine dihydrochloride (30 mg, 0.097 mmol) and 2-(4-chlorophenyl)-3-(2-methylaziridin-1-yl)propanoic acid (47 mg, 0.097 mmol) in DCM (5 mL) and TEA (1 mL). The mixture was stirred at room temperature for 1 hour. The solvent was removed, and the residue was subject to column chromatography, eluting with EA-DCM/MeOH (20:1-10:1). The product was treated with HCl (4M, 2 mL) afforded 2-(4-chlorophenyl)-1-(4-((S)-5-methyl-5,7-dihydrothieno[3,4-d]pyrimidin-4-yl)piperazin-1-yl)-3-(2-methylaziridin-1-yl)propan-1-one as the HCl salt (1 mg, 2%). LC/MS (APCI+) m/z 458.1.

Provenance & Evidence