3-Fluorophenol → HCID 53248398, compound

Participants

Reaction Conditions

Reaction Steps

(S)-1-(2-aminopyrimidin-4-yl)ethanol (6b) (7.75 g), 3-fluorophenol (6.87 g) and triphenylphosphine (16.07 g) were added to tetrahydrofuran (150 mL) under nitrogen and cooled to 0° C. (brine/ice bath). The resulting brown mixture was stirred at 0° C. for 20 min then diisopropyl azodicarboxylate (12.06 mL, 12.39 g) was added dropwise as a solution in tetrahydrofuran (40 mL). The reaction was maintained at 0-2° C. throughout the addition and was then allowed to warm to room temperature overnight. The solvent was removed under reduced pressure before the crude product was loaded onto a silica plug and purified by flash chromatography on silica eluting with heptane/ethyl acetate 7:3 followed by crystallisation from ethanol to give the title compound (6.2 g) as a white crystalline solid, MS (ES): m/z 234.0 [M+H]+; [α]D−153.0 (methanol, c=1.8 mg/ml).

Provenance & Evidence