(R)-1-(4-(trifluoromethyl)phenyl)-1,2,3,4-tetrahydroisoquinoline → (R)-N-(Pyrimidin-5-yl)-1-(4-(trifluoromethyl)phenyl)-3,4-dihydroisoquinoline-2(1H)-carboxamide

Participants

Reaction Steps

A solution of (R)-1-(4-(trifluoromethyl)phenyl)-1,2,3,4-tetrahydroisoquinoline (100 mg, 0.30 mmol, example 30 (step 1)) and 4-nitrophenyl pyrimidin-5-ylcarbamate (93.8 mg, 0.36 mmol) in MeCN (3 mL) was heated to 70° C. overnight, and then was subjected to microwave irradiation at 120° C. for 15 min. The mixture was filtered and the filtrate was purified by preparative HPLC (0%-100% MeCN 0.1% TFA/H2O 0.1% TFA) to give the title compound in solution of H2O (0.1% TFA) and MeCN (0.1% TFA). The solvent was partially removed and saturated NaHCO3 (10 mL) was added. The mixture was extracted with EtOAc (2×5 mL). The combined organic extracts were dried over MgSO4, concentrated, and dried in vacuo to give the title compound as a light yellow solid. MS (ESI, positive ion) m/z: 399 (M+H).

Provenance & Evidence