Dimethylformamide → HCID 178473713, compound

Participants

Reaction Conditions

Reaction Steps

A flask was charged with (2S,4R)-1-acetyl-6-ethynyl-2-methyl-N-2-pyrimidinyl-1,2,3,4-tetrahydro-4-quinolinamine (for a preparation see Intermediate 114) (45 mg, 0.147 mmol) and copper (I) iodide (2.80 mg, 0.015 mmol) then filled with N,N-dimethylformamide (DMF) (1.8 mL) and methanol (0.200 mL) and the resulting mixture was treated with trimethylsilyl azide (0.078 mL, 0.588 mmol). The flask was flushed with nitrogen then the mixture was stirred at 100° C. for 1 h under microwave irradiation then cooled to room temperature. Most of the methanol was removed in vacuo and the remaining organic phase was purified by MDAP (modifier: ammonium bicarbonate) to give (2S,4R)-1-acetyl-2-methyl-N-2-pyrimidinyl-6-(1H-1,2,3-triazol-4-yl)-1,2,3,4-tetrahydro-4-quinolinamine (3 mg, 8.59 μmol, 5.85% yield) as a colourless film.

Provenance & Evidence