Acetic Acid → HCID 68780522, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-[4-methoxy-6-(piperidin-4-ylamino)-[1,3,5]triazin-2-ylamino]-ethanol (0.19 g, 0.71 mmol, 1.0 equiv; intermediate C26) and 3,5-diethoxy-4-fluoro-benzaldehyde (0.17 g, 0.78 mmol, 1.1 equiv; intermediate D12) in ethanol (10 mL) under an atmosphere of Ar was added N-ethyl diisopropylamine (0.28 mL, 0.21 g, 1.63 mmol, 2.29 equiv) and glacial acetic acid (0.10 mL, 0.10 g, 1.67 mmol, 2.35 equiv) and the mixture heated to 50° C. for 2 h. After cooling down to 30° C., sodium cyanoborohydride (0.12 g, 1.91 mmol, 2.7 equiv) was added and the reaction mixture heated again to 50° C. for 1.5 h. It was then poured into crashed ice, the pH of the water phase adjusted to ˜10 by addition of a sat. solution of sodium carbonate and the mixture extracted three times with dichloromethane. The combined organic phases were washed with water, dried over MgSO4, filtered and concentrated by evaporation under reduced pressure. The crude product was purified by column chromatography on silica eluting with a gradient of dichloromethane/methanol to give 0.15 g (45%) of the title compound as light yellow oil. MS (ISP): 465.2 [M+H]+.

Provenance & Evidence