Sodium hydride → HCID 178463587, compound

Participants

Reaction Steps

3-(1-bromoethyl)-4-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-isochromen-1-one hydrobromide (C21, 100 mg, 0.233 mmol), tert-butyl 9-trityl-9H-purin-6-ylcarbamate (120 mg, 0.251 mmol) and NaH (33.6 mg, 0.699 mmol) were reacted under nitrogen at 65° C. for 2 hrs. The reaction was diluted with 15 mL of EtOAc, washed three times with 10 mL of 0.1M HClaqueous, once with saturated NaClaqueous and the solvent evaporated to give an oil. The crude was dissolved in TFA/DCM (3 mL+3 mL) and stirred for 3 h at rt and quenched by the addition of 1M HClaqueous (1 mL). The resulting mixture was straightforward purified via reverse phase chromatography using a Biotage C18 30 g SNAP with a gradient of water and acetonitrile. The combined fractions from flash chromatography were added with 1M HClaqueous (5 mL) and dried under reduced pressure to give the title compound as a yellow solid (13.6 mg, 13.3% yield) as a yellow solid.

Provenance & Evidence