Formaldehyde → HCID 73055149, compound

Participants

Reaction Steps

Formaldehyde (37% wt. in H2O; 0.017 mL, 0.22 mmol) was added to a solution of 2-(2-(2-(5-methyl-2-((6-(piperidin-4-yl)pyridin-3-yl)amino)pyrimidin-4-yl)ethyl)phenyl)acetamide (4) (32 mg, 0.07 mmol) in MeOH (4 mL) under an atmosphere of nitrogen. The resulting solution was stirred for 15 minutes at room temperature then sodium triacetoxyborohydride (63 mg, 0.30 mmol) was added in one portion. After stirring at room temperature for 18 hours a further portion of formaldehyde (37 wt. % in H2O; 0.017 mL, 0.22 mmol) was added and after 15 minutes sodium triacetoxyborohydride (63 mg, 0.30 mmol) was added in one portion. The resulting mixture was stirred at room temperature for 20 hours then the volatiles were removed in vacuo and the residue partitioned between EtOAc (50 mL) and saturated aqueous NaHCO3 (50 mL). The layers were separated and the aqueous layer was extracted with EtOAc (2×25 mL). The combined organic layers were washed with water (25 mL), brine (25 mL) and dried over Na2SO4. The volatiles were removed under reduced pressure to give the title compound 5 as an off white solid (20 mg, 61%); 1H NMR (400 MHz, d4-MeOH) δ 8.79 (d, J=2.2 Hz, 1H), 8.15 (dd, J=8.6, 2.7 Hz, 1H), 8.12 (d, J=0.6 Hz, 1H), 7.27-7.23 (m, 2H), 7.20-7.15 (m, 3H), 3.64 (s, 2H), 3.16-3.06 (m, 4H), 2.98 (dd, J=9.2, 6.0 Hz, 2H), 2.72 (tt, J=12.0, 3.9 Hz, 1H), 2.40 (s, 3H), 2.32 (td, J=12.0, 2.4 Hz, 2H), 2.11 (s, 3H), 1.97 (d, J=11.9 Hz, 2H), 1.92-1.80 (m, 2H). LCMS-A: rt 4.237 min; m/z 445 [M+H]+.

Provenance & Evidence