HCID 66600223, compound → HCID 66600163, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 6-(2-((5-fluoro-6-methoxy-3-pyridinyl)amino)-5-(1-(4-morpholinyl)ethyl)-3-pyridinyl)-N,N-bis(4-methoxybenzyl)-2-methyl-4-pyrimidinamine (0.272 g, 0.400 mmol) in TFA (3 mL) was treated with a few drops of triflic acid and heated at 80° C. for 3 h. After cooling to RT, the reaction mixture was concentrated. A few ice cubes were added and saturated NaHCO3 (aq.) was added until pH of about 7. The aqueous layer was extracted with CH2Cl2/n-BuOH (3×). The combined organic layers were dried over anhydrous Na2SO4, filtered and concentrated. The residue was adsorbed onto a plug of silica gel and purified by chromatography through a Redi-Sep pre-packed silica gel column (12 g), eluting with a gradient of 0% to 30% MeOH in CH2Cl2 to give 120 mg of 6-(2-((5-fluoro-6-methoxy-3-pyridinyl)amino)-5-(1-(4-morpholinyl)ethyl)-3-pyridinyl)-2-methyl-4-pyrimidinamine as a mixture of enantiomers as a yellow solid. 1H NMR (400 MHz, d6-DMSO) δ 12.21 (s, 1H); 8.33 (dd, J=13.01, 2.25 Hz, 1H); 8.12-8.21 (m, 2H); 7.96 (d, J=2.15 Hz, 1H); 7.04 (s, 2H); 6.79 (s, 1H); 3.92 (s, 3H); 3.57 (t, J=4.79 Hz, 4H); 3.43 (q, J=6.65 Hz, 1H); 2.51 (s, 3H); 2.38-2.47 (m, 2H); 2.27-2.36 (m, 2H); 1.34 (d, J=6.65 Hz, 3H). m/z (ESI, +ve) 440.1 (M+H)+.

Provenance & Evidence