methyl cis-5-amino-1-[4-methyl-6-(1H-pyrazol-5-ylamino)pyrimidin-2-yl]piperidine-3-carboxylate → methyl cis-1-[4-methyl-6-(1H-pyrazol-5-ylamino)pyrimidin-2-yl]-5-[({[(2S)-1,1,1-trifluoropropan-2-yl]oxy}carbonyl)amino]piperidine-3-carboxylate

Participants

Reaction Steps

The crude methyl cis-5-amino-1-[4-methyl-6-(1H-pyrazol-5-ylamino)pyrimidin-2-yl]piperidine-3-carboxylate prepared in Step 4 of Example 6 was dissolved into CHCl3 (6 ml). To the solution was added the solution of 4-nitrophenyl (2S)-1,1,1-trifluoropropan-2-yl carbonate (203.3 mg) in CHCl3 and DIEA (125.0 μl). After stirring at room temperature for 2 hours, the mixture was concentrated in vacuo. The residue was dissolved into EtOAc, poured into 1 M aqueous solution of NaOH and extracted with EtOAc. The extract was washed with saturated aqueous solution of NaHCO3, dried over MgSO4 and concentrated to give the crude methyl cis-1-[4-methyl-6-(1H-pyrazol-5-ylamino)pyrimidin-2-yl]-5-[({[(2S)-1,1,1-trifluoropropan-2-yl]oxy}carbonyl)amino]piperidine-3-carboxylate as a pale orange amorphous form.

Provenance & Evidence