Sodium Hydroxide → HCID 178503032, compound

Participants

Reaction Conditions

Reaction Steps

Ethyl 4-((S)-(4-fluorophenyl)(4-hydroxy-2-(1H-pyrazol-1-yl)pyrimidine-5-carboxamido)methyl)phenyl(methyl)phosphinate, 19-e, (12 g, 0.024 mol) was dissolved in 100 ml of dioxane and treated with 4 ml of 3N NaOH. The mixture was heated at 80° C. for one hour. The mixture was then concentrated under vacuum. The resulting residue was diluted with water and washed with ethyl acetate. The aqueous layer was acidified with conc. HCl to pH=1 and the expected product crashed out, 19-1, (9.2 g of crude). The product can be further purified via prep-HPLC (3.5 g). 1H NMR (300 MHz, DMSO-d6): δ 8.62 (s, 1H), 8.43 (s, 1H), 8.07 (s, 1H), 7.46 (m, 2H), 7.38 (m, 4H), 7.21 (m, 2H), 6.73 (s, 1H), 6.38 (d, 1H), 1.52 (d, 3H). (M+H)+=468.1.

Provenance & Evidence