Tetrahydrofuran → HCID 178472328, compound

Participants

Reaction Steps

A flask was charged with PPh3 (0.807 g, 3.08 mmol), anhydrous THF (20 mL) and DEAD (0.655 g, 3.08 mmol). The solution was stirred for 10 min under N2 then a solution of 400, THF (5 mL) and DMF (5 mL) was added and solution stirred 18 h. The solution was concentrated in vacuo to afford an orange oil. The crude product was purified by reverse phase chromatography (SP4 biotage 40M C18 using a C18 Biotage 40 samplet) and eluted with a MeCN/H2O gradient (0-60% MeCN) to afford a light yellow oil which solidified under high vacuum. The crude product was re-purified by SiO2 chromatography (SNAP 25) eluting with DCM/MeOH (95:5) to afford 0.42 g (60%) of Obtained (R)-ethyl 4-hydroxy-2-(tetrahydro-2H-pyran-4-ylamino)-6,7-dihydro-5H-pyrano[2,3-d]pyrimidine-7-carboxylate (402) as a clear oil: m/z (APCI-pos) M+1=324.0

Provenance & Evidence