Water → 4-{[(3R)-1-Benzylpiperidin-3-yl]oxy}-5-(4-ethylphenyl)-6-iodofuro[2,3-d]pyrimidine

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Reaction Steps

Add 106 mg (2.65 mmol) of sodium hydride (60% dispersion in mineral oil) to a solution of 483 mg (2.53 mmol) of (3R)-1-benzylpiperidin-3-ol [H. Tomori, Bull. Chem. Soc. Jpn. 69, 1, 207-216 (1996)] in 5 ml of THF. After stirring for ten minutes, add a solution of 1020 mg (70% purity, 1.86 mmol) of 4-chloro-5-(4-ethylphenyl)-6-iodofuro[2,3-d]pyrimidine in 5 ml of THF and 47 mg (0.13 mmol) of tetra-n-butylammonium iodide. Stir the reaction mixture at room temperature for five hours. After adding water and ethyl acetate, wash the removed organic phase with 1N hydrochloric acid and satd. sodium chloride solution and then concentrate under reduced pressure. Take up the residue in acetonitrile and purify by means of preparative RP-HPLC (gradient: water/acetonitrile). 266 mg (20% of theory) of the desired product are obtained.

Provenance & Evidence