Triphenylphosphine → 2-Pyrimidineethanamine, beta,beta-difluoro-

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Reaction Steps

A portion of the 2-(2-azido-1,1-difluoro-ethyl)-pyrimidine (578 mg, 3.12 mmol) was taken up in THF (8 mL), 0.1 M NaOH (aq) (0.6 mL), and PPh3 (982 mg, 3.74 mmol) and stirred at 50° C. for 29 h. The resulting pale yellow solution was allowed to cool to rt, dried (2×Na2SO4), and treated with 4 M HCl/dioxane (2 mL; approximately 8 mmol HCl). The precipitate was collected by decantation, and washed with dry ether (3×15 mL). The solid was then partitioned with 4 M NaCl (4 mL) and EtOAc (4 mL), and the aqueous layer was washed with EtOAc (1×4 mL). The aqueous layer was then brought to a pH greater than 10 with 2.5 M NaOH, and extracted with equal volumes of DCM (3×5 mL). The combined organic layers were dried (Na2SO4) and concentrated under rotary evaporation at 35° C. to provide the title compound as a pale yellow oil (419 mg, 85% over two steps).

Provenance & Evidence