Formaldehyde → HCID 72944105, compound

Participants

Reaction Conditions

Reaction Steps

Sodium triacetoxyborohydride (50 mg; 0.24 mmol; 2.0 eq.) was added to a solution of 2-[3-(1-methyl-1H-pyrazol-4-yl)phenyl]-5-(1-piperidin-4-yl-1H-pyrazol-4-yl)pyrimidine (example 1, 50 mg; 0.12 mmol; 1.0 eq.), formaldehyde (16 μl of a 36% aq. solution; 0.21 mmol; 1.8 eq.) and DIEA (24 μl; 0.14 mmol; 1.2 eq.) in DCE (2 mL). The reaction mixture was heated at 50° C. for 1 hour. It was then diluted with DCM and poured into a saturated solution of NaHCO3. The organic phase was washed with brine, dried over magnesium sulfate, filtered and concentrated to give the title compound as a white solid (25 mg; 53%). 1H NMR (300 MHZ, DMSO-d6) δ 9.17 (s, 2H), 8.54-8.52 (m, 2H), 8.26 (s, 1H), 8.22 (dt, J=7.8 Hz, 1.5 Hz, 1H), 8.15 (s, 1H), 7.92 (d, J=1.5 Hz, 1H), 7.51 (dt, J=7.8 Hz, 1.5 Hz, 1H), 7.51 (t, J=7.8 Hz, 1H), 4.31-4.20 (m, 1H), 3.89 (s, 3H), 3.04-3.01 (m, 2H), 2.36-2.23 (m, 5H), 2.10-2.03 (m, 4H). HPLC (Condition A): Rt 2.48 min (purity 99.3%). MS (ESI+): 400.50.

Provenance & Evidence