Sodium Hydroxide → HCID 178503027, compound

Participants

Reaction Conditions

Reaction Steps

Ethyl ((S)-(4-hydroxy-2-(1H-pyrazol-1-yl)pyrimidine-5-carboxamido)(phenyl)methyl)phenyl(methyl)phosphinate, 25-e, (33 g, 69 mmol) was dissolved in 400 ml of dioxane and treated with 100 ml of 3N NaOH. The mixture was heated at 80° C. for one hour. The mixture was then concentrated under vacuum and the 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, 25-1, (11 g of crude). The product can be further purified via prep-HPLC. 1H NMR (300 MHz, DMSO-d6): δ 10.39 (br, 1H), 8.62 (s, 1H), 8.45 (s, 1H), 8.07 (s, 1H), 7.37 (m, 9H), 6.73 (s, 1H), 6.33 (d, 1H), 1.52 (d, 3H). (2M+H)+=899.0.

Provenance & Evidence