1-Butanol → (S)-Methyl 2-(3-((2-amino-4-(1-hydroxyhexan-3-ylamino)-6-methylpyrimidin-5-yl)methyl)-4-fluorophenyl)acetate

Participants

Reaction Conditions

Reaction Steps

Aq. 5M KOH (0.5 mL) was added to a stirred solution of the product from step (v) (70 mg) in butan-1-ol (1 mL) and heated to 100° C. for 15 h. The mixture was allowed to cool, diluted with water (2 mL) and then adjusted to ˜pH 7 with conc. HCl. The organic phase was separated and the aqueous was extracted with butan-1-ol (5 mL). The combined organic extracts were evaporated, the residue was dissolved in MeOH and conc. HCl (0.3 mL) was added and the mixture heated to 70° C. for 1 h. After cooling the reaction was poured into sat. NaHCO3 (10 mL) and extracted with EtOAc, dried and the solvent removed. The crude product was purified by RPHPLC to afford the title compound as a colourless gum, 22 mg.

Provenance & Evidence