Formic Acid → (3R)-3-{[5-(4-Ethylphenyl)-6-(2-fluorophenyl)furo[2,3-d]pyrimidin-4-yl]oxy}piperidinium formate

Participants

Reaction Steps

Add 30 mg of 10% palladium on activated carbon to an argon-blanketed solution of 275 mg (0.54 mmol) of 4-{[(3R)-1-benzylpiperidin-3-yl]oxy}-5-(4-ethylphenyl)-6-(2-fluorophenyl)furo-[2,3-d]pyrimidine in 5 ml of methanol/ethanol (1:2), and stir at room temperature under a hydrogen atmosphere (standard pressure) for three hours. After adding a further 70 mg of 10% palladium on activated carbon, stir the reaction mixture for another 19 hours under a hydrogen atmosphere (standard pressure) at room temperature. Add a further 175 mg of 10% palladium on activated carbon and 0.2 ml of formic acid, and stir the reaction mixture once again at room temperature under a hydrogen atmosphere (standard pressure) for 15 hours. After filtering off the catalyst, wash the catalyst residue with methanol/water. Concentrate the filtrate under reduced pressure, take up the residue in acetonitrile/DMSO and purify by means of preparative RP-HPLC (gradient: water/acetonitrile/formic acid). 137 mg (54% of theory) of the desired product are obtained.

Provenance & Evidence