Acetonitrile → HCID 118453815, compound

Participants

Reaction Steps

A mixture of 4-(4-amino-5-((benzyloxy)methyl)-2-butyl-5H-pyrrolo[3,2-d]pyrimidin-7-yl)butan-1-ol (884 mg, 2.311 mmol), N-methylmorpholine N-Oxide (420 mg, 3.59 mmol), powdered 4 Å molecular sieves and tetrapropylammonium perruthenate (58 mg, 0.165 mmol) was placed under nitrogen and a mixture of anhydrous dichloromethane (27 mL) and anhydrous acetonitrile (3 mL) added. The reaction mixture was stirred at ambient temperature for 2 hours, Additional N-methylmorpholine N-Oxide (390 mg, 3.33 mmol) and tetrapropylammonium perruthenate (38 mg, 0.108 mmol) in anhydrous DCM (5 mL) was added and the reaction mixture stirred at ambient temperature for a further 2 hours. Additional N-methylmorpholine N-Oxide (130 mg, 1.11 mmol) and tetrapropylammonium perruthenate (100 mg, 0.284 mmol) were added and the reaction mixture stirred at ambient temperature for a further 30 mins, The reaction mixture was filtered through Celite and the cake washed with DCM three times. The reaction solvent was removed in vacuo and the residue dissolved in DCM and passed through Celite a second time. The cake was washed with DCM three times and the solvent removed in vacuo to give a black gum. The sample was dissolved in dichloromethane and purified by chromatography on on silica (100 g) using a gradient of 0-25% methanol-dichloromethane over 40 mins. The appropriate fractions were combined and evaporated in vacuo to give an orange gum with a black tinge. The sample was dissolved in dichloromethane and purified by chromatography on on silica (100 g) using a gradient of 0-25% methanol-dichloromethane over 80 mins. The appropriate fractions were combined and evaporated in vacuo to give the title compound as a pale yellow gum (268 mg).

Provenance & Evidence