Water → 2-(Aminomethyl)-7,8-dihydro-3H-pyrano[4,3-D]pyrimidin-4(5H)-one

Participants

Reaction Steps

To a solution of 2-(azidomethyl)-7,8-dihydro-3H-pyrano[4,3-d]pyrimidin-4(5H)-one (19 g, 92 mmol) in THF (945 mL) at 35° C. was added triphenylphosphine (26.5 g, 101 mmol). Gas evolution was noted immediately and after approximately 40 minutes a fine precipitate formed. The reaction was allowed to stir for 1.5 h then 18.17 mL water was added. After an addition 2 h the reaction mixture was cooled to room temperature, filtered twice, concentrated to approximately ⅓ of the original volume and filtered once more. The solid material was washed with THF to yield a total of 15.82 g of the title compound. 1H NMR (400 MHz, MeOD) δ ppm 2.66 (t, J=5.56 Hz, 2H) 3.76 (s, 2H) 3.94 (t, J=5.56 Hz, 2H) 4.49 (s, 2H)

Provenance & Evidence