Diethyl Ether → 2-(5-(4-Amino-6-methyl-1,3,5-triazin-2-YL)-6-(5-(phenylsulfonyl)pyridin-3-ylamino)pyridin-3-YL)propan-2-OL

Participants

Reaction Conditions

Reaction Steps

To cerium(III) chloride (304 mg, 1.235 mmol) was added THF (4.1 mL) and the resulting mixture was heated to 40° C. for 1 h. The reaction mixture was then cooled to −78° C. and methylmagnesium bromide in ether (3.0 M, Aldrich; 1372 μL, 4.12 mmol) was added. The resulting mixture was stirred at −78° C. for 15 min. 1-(5-(4-Amino-6-methyl-1,3,5-triazin-2-yl)-6-(5-(phenylsulfonyl)pyridin-3-ylamino)pyridin-3-yl)ethanone (190 mg, 0.412 mmol) in THF (4.1 mL) was then added, and the resulting mixture was stirred at −78° C. for 4 h. The reaction mixture was subsequently diluted with 100 mL of EtOAc, added to a separatory funnel, and partitioned with sodium bicarbonate (saturated, aqueous). The organic layer was separated, washed 2 times with 50 mL of sodium bicarbonate (saturated, aqueous), dried over sodium sulfate, and concentrated in vacuo. Chromatographic purification of the residue (silica gel, 0% to 3% (2 M ammonia in MeOH)/DCM) provided the title compound (36% yield) as a light yellow solid. 1H NMR (400 MHz, d6-DMSO) δ 12.38 (s, 1H) 9.18-9.23 (m, 1H) 9.06 (d, J=2.35 Hz, 1H) 9.00 (d, J=2.35 Hz, 1H) 8.67 (d, J=2.15 Hz, 1H) 8.53 (d, J=2.54 Hz, 1H) 8.02-8.08 (m, 2H) 7.98 (br. s., 1H) 7.79 (br. s., 1H) 7.71-7.77 (m, 1H) 7.64-7.71 (m, 2H) 5.22-5.26 (m, 1H) 2.46 (s, 3H) 1.51 (s, 6H). m/z (ESI, +ve ion) 478.1 (M+H)+.

Provenance & Evidence