Hydrochloric Acid → HCID 178492171, compound

Participants

Reaction Steps

6-(6-methoxypyridin-3-ylamino)-5-(2-methyl-9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-yl)nicotinaldehyde (90.6 mg, 0.203 mmol) was suspended in ethanol (1.2 mL) and DCM (1.2 mL), and isopropylamine (0.060 mL, 0.70 mmol) and tetraisopropoxytitanium (0.20 mL, 0.68 mmol) were added. The reaction was stirred at room temperature for 75 min, and then sodium borohydride (26.8 mg, 0.708 mmol) was added, along with MeOH (1 mL), and stirring was continued at room temperature. After 2 h, more MeOH and 5 N HCl (0.50 mL) were added, and stirring was continued overnight. The suspension was diluted with DCM and MeOH and filtered through a Celite® (diatomaceous earth) pad, which was washed with DCM and MeOH. The filtrate was concentrated and purified by prep HPLC to give 5-((isopropylamino)methyl)-N-(6-methoxypyridin-3-yl)-3-(2-methyl-9H-purin-6-yl)pyridin-2-amine (79.5 mg, 97.1% purity, 76% yield) as a TFA salt. 1H NMR (d6-DMSO, 400 MHz) δ 12.71 (br s, 1H), 9.80 (br s, 1H), 8.69 (s, 1H), 8.65 (br s, 2H), 8.58 (d, J=2.74 Hz, 1H), 8.42 (d, J=2.15 Hz, 1H), 8.14 (dd, J=9.00 Hz, 2.74 Hz, 1H), 6.89 (d, J=9.00 Hz, 1H), 4.24-4.18 (m, 2H), 3.86 (s, 3H), 3.48-3.38 (m, 1H), 2.87 (s, 3H), 1.31 (d, J=6.46 Hz, 6H). m/z (ESI, +ve ion) 405 (M+H)+.

Provenance & Evidence