Benzeneethanamine, alpha-methyl-, phosphate (1:1) → (R)-7'-(3,6-dihydro-2H-pyran-4-yl)-3'-fluoro-2'-(pyrimidin-5-yl)-5H-spiro[oxazole-4,9'-xanthen]-2-amine

Participants

Reaction Conditions

Reaction Steps

A mixture of 5-(tributylstannyl)pyrimidine (73.8 mg, 0.200 mmol), AmPhos (4.24 mg, 5.99 μmol) and (R)-2-amino-2′-(3,6-dihydro-2H-pyran-4-yl)-6′-fluoro-5H-spiro[oxazole-4,9′-xanthene]-7′-yl trifluoromethanesulfonate (50 mg, 0.100 mmol) in 0.3 mL of DMF was heated at 130° C. for 1 hour. After cooling and evaporation of the solvent under high vacuum, the mixture was purified by silica gel chromatography (DCM to DCM/EA=1:1 to 1:2 to pure EA to EA/MeOH=100:5 to 100:10) to provide (R)-7′-(3,6-dihydro-2H-pyran-4-yl)-3′-fluoro-2′-(pyrimidin-5-yl)-5H-spiro[oxazole-4,9′-xanthen]-2-amine as an off-white solid.

Provenance & Evidence