Ammonia → HCID 59548416, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 1-(methylsulfonyl)piperazine (5.61 mg, 0.034 mmol, Apollo), 1-(6-(6-amino-2-methylpyrimidin-4-yl)-5-(6-methoxypyridin-3-ylamino)pyrazin-2-yl)ethanone (6 mg, 0.017 mmol) and tetraisopropoxytitanium (19.41 mg, 0.068 mmol, Aldrich) in tetrahydrofuran (0.5 mL) was stirred at 75° C. for 48 h. The mixture was cooled down to 20° C. and CH2Cl2 (1 mL) was added followed by sodium triacetoxyborohydride (14.48 mg, 0.068 mmol). The reaction mixture was stirred at room temperature for 5 h. Ammonia (1 mL, 30% in water) was added and the mixture was extracted with CH2Cl2 (2×10 mL). The combined organic extracts were washed with saturated NaCl (5 mL) and dried over Na2SO4. The solution was filtered and concentrated in vacuo to give the crude material as a yellow solid. The crude product was purified by silica gel chromatography eluting with 5% MeOH/CH2Cl2 to give 6-(3-(6-methoxypyridin-3-ylamino)-6-(1-(4-(methylsulfonyl)piperazin-1-yl)ethyl)pyrazin-2-yl)-2-methylpyrimidin-4-amine (5.2 mg, 10.41 μmol, 61.0% yield). 1H NMR (300 MHz, CDCl3) δ 1.48 (d, J=6.87 Hz, 3H) 2.64 (s, 3H) 2.78 (s, 4H) 3.14-3.40 (m, 4H) 3.81 (q, J=6.72 Hz, 1H) 5.10 (s, 2H) 6.78 (d, J=8.77 Hz, 1H) 7.46 (s, 1H) 8.08 (dd, J=8.84, 2.70 Hz, 1H) 8.20 (s, 1H) 8.43 (d, J=2.63 Hz, 1H). m/z (ESI, +ve ion) 500.1 (M+H)+.

Provenance & Evidence