Sodium triacetoxyborohydride → HCID 178503378, compound

Participants

Reaction Steps

A mixture of 4-[2-(methylthio)-6-phenylpyrido[2,3-d]pyrimidin-7-yl]benzaldehyde (1-4) (0.200 g, 0.56 mmol), 2-(3-piperidin-4-yl-1H-1,2,4-triazol-5-yl)pyridine HCl salt (A [see synthesis below]; 0.193 g, 0.727 mmol), and TEA (0.074 g, 0.727 mmol) were stirred in 5% AcOH in DMF for 0.5 hr. Sodium triacetoxyborohydride (0.178 g, 0.0.839 mmol) was then added and the reaction was stirred for 3 hr. The reaction was quenched with 3N NaOH and extracted 3×w/CH2Cl2. The combined organics were dried (anhd. Na2SO4), filtered, and concentrated. The residue was purified by silicon gel chromatography (6% MeOH in CH2Cl2) to give the titled compound. 1H-NMR (500 MHz, d6 DMSO) δ 9.50 (s, 1H), 8.64-8.72 (m, 2H), 8.58 (s, 1H), 7.88-8.07 (m, 3H), 7.28-7.56 (m, 9H), 3.52 (s, 2H), 2.84 (m, 2H), 2.66 (s, 3H), 2.11 (m, 3H), 1.96 (m, 2H), 1.78 (m, 2H). LRMS m/z (M+H) calcd: 571.7, found: 571.2.

Provenance & Evidence